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Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives

Our starting alkenes 4al are original and were synthesized in four steps involving coupling, Grignard, oxidation, and Wittig reactions. We synthesized the novel unactivated alkenes 4al containing three aryl groups as the starting materials. The synthesis of 4a is demonstrated in Scheme 1. First, 2-phenoxybenzaldehyde (1a) was synthesized by coupling reaction of phenol with commercial 2-fluorobenzaldehyde. This reaction was carried out with very high yield by refluxing the reactants in the presence of K2CO3 in DMF.


2-Phenoxybenzaldehyde (1a) was converted into secondary alcohol derivative 2a by adding a phenyl group using a Grignard reaction. This reaction was carried out with high yield by adding the freshly prepared Grignard compound of phenyl bromide to 2-phenoxybenzaldehyde. As a result, phenoxy secondary alcohol 2a containing three aromatic rings was obtained. In the third step, 2a was oxidized and the ketone derivative 3a was obtained in high yield. The oxidation reaction was carried out using PCC in DCM at room temperature. In the fourth and final step, phenoxydiphenylalkene derivative 4a was prepared by a Wittig reaction, which was carried out using methyltriphenylphosphonium bromide with ketone 3a, in basic medium, at room temperature, and dry THF.

After the structures of the starting compounds were elucidated, the method development trials for the synthesis of xanthene derivatives were carried out. For this purpose, catalyst researches were carried out using compound 4a. An intramolecular Friedel–Crafts reaction was tried by activating the alkene with various organic Brønsted acids and Lewis acids (Table 1). In the reaction, iron(III) chloride hexahydrate, trifluoroacetic acid (TFA), N-trifylphosphoramide (NTPA), benzoic acid, diphenyl phosphate (DPP), malonic acid, chloroacetic acid, copper(II) triflate, acetic acid, and p-toluenesulfonic acid (p-TSA) were used as catalysts. TFA gave the best yield of these catalysts with 78% (Table 1, entry 2). The second-best yield was 65% when FeCl3·6H2O was used (Table 1, entry 1).

[Graphic 1]
Entry Catalyst (10 mol %) Conv. (%)b
1 FeCl3·6H2O 65
3 NTPA 10
4 benzoic acid 0
5 DPP 2
6 malonic acid 0
7 chloroacetic acid 14
8 Cu(OTf)2 12
9 AcOH 0
10 p-TSA 3

aConditions: 4a (0.1 mmol) and catalyst (10 mol %) in CHCl3 (1 mL) were stirred at room temperature for 24 hours. bConversions were determined with GC–MS.

Then the solvent was investigated. Toluene, methyl alcohol, ethyl acetate, THF, DMF, dichloromethane, chloroform, acetone, and acetonitrile were tested as solvents. As a result, it was determined that the best conversion was with dichloromethane (Table 2). Later, quantity and time experiments were performed (Table 2, entries 10–15) and, at the end of these trials, it was determined that the reaction was completed with >99% conversion in 6 hours with 10 mol % catalyst at room temperature (Table 2, entry 14).

[Graphic 2]
Entry Cat. amount (mol %) Solvent Time Conv.b
1 10 CHCl3 24 h 78
2 10 acetone 24 h 75
3 10 toluene 24 h 70
4 10 CH2Cl2 24 h >99
5 10 THF 24 h 45
6 10 CH3CN 24 h 10
7 10 MeOH 24 h 0
8 10 EtAc 24 h 35
9 10 DMF 24 h 0
10 10 CH2Cl2 1 h 32
11 10 CH2Cl2 2 h 53
12 10 CH2Cl2 3 h 70
13 10 CH2Cl2 4 h 85
1410CH2Cl26 h>99
15 5 CH2Cl2 6 h 95

aConditions: 4a (0.1 mmol) and TFA in dry solvent (1 mL) were stirred at room temperature. bConversions were determined with GC–MS.

After determining the most suitable conditions for the intramolecular Friedel–Crafts reaction with alkene activation, the synthesis of the new xanthene derivatives was performed according to this method. The synthesized xanthene derivatives with their isolated yields are shown in Figure 1. Compounds 5bl were synthesized for the first time in this study. The first synthesis of 5a was prepared by reduction of the corresponding xanthydrol [53] and was also synthesized recently by a different method from our group [29].


Although in the reactions for FCA reagents and strong inorganic acids, such as AlCl3, H2SO4, or H3PO4, which have generally corrosive properties, were used, in this study, an intramolecular ring closure reaction was carried out under easy operating conditions with an organic Brønsted acid catalyst with high yields. So, the xanthene synthesis with alkene activation was performed for the first time using TFA. The reasonable mechanism of this reaction is delineated in Scheme 2.


Despite this reaction occurring by the classical Friedel–Crafts mechanism, we believe that o-quinone methide is formed as an intermediate. Because of its very reactive structure, most of the xanthene synthesis is based on the o-quinone methide intermediate [54-58]. The carbocation formed by the activation of an alkene with acid turns into an intermediate o-quinone methide, resulting in a successful cyclization.

As seen in the mechanism, the acid catalyst adds to the vinyl group, allowing the formation of a tertiary carbocation. The carbocation is then transformed into the o-quinone methide intermediate, which undergoes cyclization to yield 9-methyl-9-arylxanthene by aromatization. When the yields of the synthesized compounds are examined, it is seen that the yields are high when there is no substituent at the ring to which the carbocation is attached or when there is an electron-donating group, such as a methoxy or methyl group (Figure 1). When there are electron-withdrawing groups, such as chlorine or cyano groups, in the ring, the yield is slightly reduced because they deactivate the ring in the transition state. The lowest yield was observed for compound 5j to which a cyclopentyl group is attached. Since the cyclopentyl group in this compound is directly attached to the carbon from which the carbocation is formed, byproducts are formed and the yield is reduced since conversions can occur.


Types of talking therapy

Talking therapies are psychological treatments for mental and emotional problems like stress, anxiety and depression.

There are lots of different types of talking therapy, but they all involve working with a trained therapist.

This may be one-to-one, in a group, online, over the phone, with your family, or with your partner.

The therapist helps you find answers to the problems you're having.

For some problems and conditions, one type of talking therapy may be better than another.

Different talking therapies also suit different people.

Talking therapies on the NHS

You can get talking therapies like counselling for depression and cognitive behavioural therapy (CBT) on the NHS.

You can refer yourself directly to an NHS psychological therapies service (IAPT) without a referral from a GP.

Find an NHS psychological therapies service (IAPT)

If you prefer, see a GP and they can refer you and share relevant information about you.

Psychological therapies services are also known as Improving Access to Psychological Therapies (IAPT) services.

Cognitive behavioural therapy (CBT)

The aim of CBT is to help you explore and change how you think about your life, and free yourself from unhelpful patterns of behaviour.

You set goals with your therapist and may carry out tasks between sessions.

A course usually involves around 12 to 20 sessions.

CBT has been shown to work for a variety of mental health problems, including:

CBT is available on the NHS for people with depression, anxiety disorders and other mental health problems that it's been proven to help.

Read more about talking therapies on the NHS.

There are also self-help books and computer courses based on CBT to help you overcome common problems like depression.

Find out more about CBT

Guided self-help

Guided self-help is recommended as a treatment for depression, anxiety and panic disorder.

With guided self-help you work through a CBT-based workbook or computer course with the support of a therapist.

The therapist works with you to understand your problems and make positive changes in your life.

Guided self-help aims to give you helpful tools and techniques that you can carry on using after the course has finished.

During the course your therapist will support you with face-to-face appointments or phone calls.

See some more self-help therapies.


Counselling is a talking therapy where you talk in confidence to a counsellor. They help you find ways to deal with difficulties in your life.

You may be offered counselling on the NHS if, for example, you:

  • are struggling to cope with a long-term condition
  • have chronic pain
  • have an addiction
  • are having fertility problems

Counselling on the NHS usually consists of 6 to 12 sessions.

Read more about counselling.

Counselling for depression

Counselling for depression has been specially developed to help people understand the underlying causes of their depression.

Counselling for depression is available through psychological therapies services.

It's usually offered to people who have mild to moderate depression and have already tried other therapies, such as guided self-help.

Behavioural activation

Behavioural activation is a talking therapy that aims to help people with depression take simple, practical steps towards enjoying life again.

It may be offered one-to-one or in a group with regular meetings or phone calls with a therapist.

The aim is to give you the motivation to make small, positive changes in your life.

You'll also learn problem-solving skills to help you tackle problems that are affecting your mood.

You'll usually be offered about 16 to 20 sessions.

Interpersonal therapy (IPT)

IPT is a talking treatment that helps people with depression identify and address problems in their relationships with family, partners and friends.

The idea is that poor relationships with people in your life can leave you feeling depressed.

Depression can in turn make your relationships with other people worse.

You may be offered IPT if you have severe depression or depression that hasn't responded to other talking therapies, such as CBT.

IPT is usually offered over 16 to 20 sessions.

Eye movement desensitisation and reprocessing (EMDR)

EMDR is another talking therapy that's been developed to help people who have post-traumatic stress disorder (PTSD).

People who have PTSD may experience intrusive thoughts, memories, nightmares or flashbacks of traumatic events in their past.

EMDR helps the brain reprocess memories of the traumatic event so you can let go of them.

EMDR can be a distressing process, so it's important to have a good support network of family and friends around you if you plan to try it.

A course of treatment is likely to be 8 to 12 sessions.

Mindfulness-based cognitive therapy (MBCT)

Mindfulness-based therapies help you focus on your thoughts and feelings as they happen moment by moment.

They can be used to help treat depression and addiction.

Mindfulness-based cognitive therapy (MBCT) combines mindfulness techniques like meditation and breathing exercises with cognitive therapy.

MBCT is one of the options that may be offered to you after a course of treatment for depression to help stop it coming back.

Read more about mindfulness.

You can find mental health apps and tools in the NHS apps library.

Video: Psychological therapies for stress, anxiety and depression

Animated video explaining self-referral to psychological therapies services for stress, anxiety or depression.

Media last reviewed: 1 September 2021
Media review due: 1 September 2024


Online license activation

Offline (manual) license activation

To use Unity, you need an activated licence. For Unity Plus and Pro licenses, you need to get a serial number; for a Unity Personal license, you don’t need a serial number. To see what kinds of licences Unity offers, go to the Unity Store.

Tip: You should always sign into the Unity ID dashboard in order to access anything you purchased from the Asset StoreA growing library of free and commercial assets created by Unity and members of the community. Offers a wide variety of assets, from textures, models and animations to whole project examples, tutorials and Editor extensions. More info
See in Glossary, or any licenses your Organization granted you. If you don’t have a Unity ID yet, open the Unity ID dashboard to create one.

To activate a Unity Personal license, you must go to the Unity Hub and answer some questions about your situation and for what purposes you plan to use Unity. For more information, see Activating a licence in the Hub.

To activate a Unity Plus or Pro license, you need to provide the serial number for the machine you want to activate it on. For single licenses, Unity emails the license information and serial number to the purchaser.

If you don’t know your Unity license information, speak to the Owner of your license. Owners can assign a seat to you via the Organization, or you can contact Unity Customer Service.

You can activate your license either through the Unity Hub or the command line:

Activating a licence in the Hub

If you haven’t installed the Hub yet, you can download it from the Download Unity web page. Then follow these steps:

  1. Select the Settings button from the top right of the Hub. The Preferences window appears.

  2. Select License Management from the list on the left.

    Hub > Preference > License Management
  3. If you see a message at the bottom of the window warning you that you need to be logged in to manage your license, select the LOGIN button from the bottom right and then enter your Unity ID and password.

    Important: You can’t activate your license in the Unity Hub unless you are signed into your Unity ID.

  4. Select the ACTIVATE NEW LICENSE button. The New License Activation window appears.

    New licence activation window
  5. Select which license type you are activating:

    • If you select the Unity Personal option, you must select either of the options which best describes your current situation and click Done.
    • If you select the Unity Plus or Pro option, enter the Serial Number you received in an email when you purchased a single license. You need to enter the key in the exact format that it appears in the email. For example, .

    Note: To activate an educational license select the Unity Plus or Pro option.

  6. Click DONE. Unity displays a success message.

If Unity displays an error message that the license activation was not successful, check Activation issues to find a solution for your issue.

Activating a license from the command line

Before activating your Unity license on the command line, make sure that the license file folder exists and you have write permission.

Note: The command line procedure only works for Plus and Pro licenses because Personal licenses do not have serial numbers associated with them. Use the Unity Hub to activate Personal licenses.

On macOS, enter the following into the Terminal to launch Unity and activate your license:

Replace with the actual path to your Editor installer. Typically, this is usually something like on macOS.

Tip: If you use continuous integration (CI) tools like Jenkins to activate via the command line, add the flag to prevent a WindowServer error.

On Windows, enter the following into the Command Prompt to launch Unity and activate your license:

Replace with the actual path to your Editor installer. Typically, this is usually something like on Windows.

Wait a few seconds after running this command to give Unity enough time to communicate with the license server. If activation fails, you can open the Editor.log for information. For any activation errors, check Activation issues to find a solution for your issue.

Offline (manual) license activation


Microsoft Office 2019 Activation Key + Crack ISO Free Download

Microsoft Office 2019 Activation Key + Crack ISO Free Download

Microsoft Office 2019 Activation Key is a cross-platform that is comprehensive for everyone with smart tools for specific users, teams, and businesses. It can open your apps, documents anywhere on numerous products. It offers brand new compliance and deployment protection, giving companies more significant control of sensitive data and greater flexibility in deployment and management. Microsoft has expanded offices for iPad and Android pills. Updated Office features on Mac, iPhone, plus the web.

Additionally, brand new applications have been added to your family, a swipe and office lens. All things are made to keep work everywhere. We have concentrated on customizing Office for different platforms in the last 12 months. Office on the Windows desktop is Central to our strategy when you’ve seen just how.

Microsoft Office 2019 Crack is the latest version. It is the most demanded software ever. Everyone uses MS Office for their projects. Simply put, now you can’t do anything without Microsoft Office 2019 Crack. And one of the many difficulties that primary users can’t activate this version quickly. For sure, the user needs the Microsoft Office 2019 activation key for the activation of the software. So then you will solve your problem on this important platform if you’re certainly one of them. Right here, you’ll find working and activation that is valid for lifetime activation.

Microsoft Office 2019 Crack Download Full ISO

Microsoft Office 2019 Crack is utterly appropriate for its wide range – from students to office staff and personnel, along with business professionals. Due to the different enhancements, the essential functions, and the development of new people, document creation, processing, and handling are now doable and faster than previously. In addition, mathematical calculations and expressions are improved and generally are far more easily incorporated into practical use within PowerPoint 2016, Excel 2016, and Word 2016.

Microsoft Office 2019 Activation Key is useful for both Windows as well as a Mac users. It can open, edit, make, and save files regarding the cloud from your desktop. And a search that is new for commands is available in MS PowerPoint, Excel, and Outlook. Updated choices include its user software that supports Retina Display and uses ribbons as well. In addition, users can now share documents via social networks and email messages directly through the MS Office 2016 Crack toolbar.

Key Features of Microsoft Office 2019 Crack:

  • Better along with Windows 10– allow you to complete work, the papers in full fidelity across your Windows 10 products.
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  • You are permitted by the application to enter everything you wish to do in your terms, then guide you on how best to do so – plus other resources.
  • Modern shapes benefit from newly redesigned forms in Visio professionals.
  • Real-time typing-view everyone’s edits and where these are typically into the document as you work simultaneously on the same document.
  • New chart types– present better visualization ability and enables you to identify the partnership that is statistical your computer data.
  • Improved data connectivity-connecting your diagram to Excel data is just one click away.
  • Themes – the latest themes give a fresh look and an amazing presentation.
  • Smart lookup checks your document and automatically teaches you the SERPs via your writing environment via the web.
  • One drive integration – enables you to store your details in one access and location other than anywhere, using any device.

What’s New in Microsoft Office 2019 Crack?

  • Powerpoint, one notes, Skype, PowerPoint, Access, Excel, Skype, and Outlook are the most popular and advanced applications.
  • Creates presentations and creates computer analysis records.
  • Tests the emails from Outlook.
  • It does not need VPN settings from anywhere to call.
  • In the layout parameter, it will also automatically customize the UI.
  • All papers, including PDF e-books, are very much sponsored.
  • Updates and edits the database and prints a selection of templates as well.
  • Use Excel to create tables and solve problems with mathematics.
  • It can also view and edit device-wide files.
  • Create amazing Microsoft PowerPoint 2019 presentations.
  • Besides, we can work on the same project with our team concurrently.
  • Get permission automatically and post the reports with one touch.
  • New charts for displaying nuanced details are also included.

Microsoft Office 2019 Activation Key







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Benefits of Using Microsoft Office 2019 Activation Key?

Also, several individuals will concurrently work on the paper or an Excel spreadsheet or PowerPoint. This functionality was updated by Microsoft and is gradually being marketed now. Not everybody will be compelled to go to the cloud, but there’s a lot of push with subscription providers. And one thing to do is, even now, the Office 365 Crack has such a feature as more, for example, or PowerPoint concept concepts, which are not routinely available for the Office 2016 Crack. It is a database adapted so that certain features bring users into the cloud. Office 2019 presents lots of new features and some of the coolest I’ll introduce. Many of them are not exactly new functions. But they were exclusive to office 365, so you can now get access to them if you do not want to pay the monthly fee.

Microsoft Office 2019 Keys


Microsoft Office 2019 Product Key


Installation Instructions for Office 2019 Crack:

  1. The download is given below to start.
  2. Extract zip file through WinZip.
  3. Click “setup” and proceed with the installation process.
  4. Complete configuration and close it.
  5. Open MS Toolkit located inside the crack directory.
  6. Click the button to the left of the Windows icon and go to the Service tab.
  7. Activate” Microsoft Office 2019.
  8. Done!


PDF-XChange Editor has more than 250 features that you can use to perform a huge range of operations on PDF documents, as detailed below.

New Features Added in Version 9.2.357.0

File Extension Macro Added

File Extension Macro Added

A new File Extension macro is now available in PDF-XChange Editor and can be used to output the file extension of documents.

Font Customization for the Summarize Comments Feature

Font Customization for the Summarize Comments Feature

Font customization is now available for the summarize comments operation in PDF-XChange Editor.

New Rendering Modes Implemented for 3D Models

New Rendering Modes Implemented for 3D Models

New rendering modes are now available for 3D content in PDF-XChange Editor.

Open and Convert WebP Format Images to PDF

Open and Convert WebP Format Images to PDF

PDF-XChange Editor can now be used to open and convert to PDF images that are saved in WebP format.

Print All Open Documents

Print All Open Documents

Print All feature is now available in PDF-XChange Editor that allows you to print all open documents.

Print Portfolios

Print Portfolios

It is now possible to print PDF portfolio files in PDF-XChange Editor.

Select Highlighted Text

Select Highlighted Text

It is now possible to select text that is already highlighted in documents with PDF-XChange Editor.

Updates to User Interface

Updates to User Interface

New themes for the user interface are available in this build of PDF-XChange Editor, and the default UI has been updated to a new style.

Numerous Additional Bug Fixes and Improvements

Numerous Additional Bug Fixes and Improvements

As usual, a range of features, improvements and bug fixes have been made in this release of your favourite software for the viewing, editing and creation of PDF documents - PDF-XChange Editor. Please see the Version History for further information.


Windows 10 Product Key Crack With Serial Number Free Download 2022

Windows 10 Crack Product Key 64/32 Bit Torrent + [100% Working]

Windows 10 Crack provides a product key for each user. A product key is the user’s century-old code for product authenticity created for each user. they may ask you to enter your product key. If your product is not available, you will need to crack Windows 10 to activate it. There are several Windows 10 hacks through which you can easily break windows to activate it.

Windows 10 64/32 Bit operating system has received an excellent set of tools for its flexible functions and wide choice. Windows 10 was unexpectedly released a long time ago in this already launched market. Users downloaded over a million copies on a single opening day. Windows has demonstrated satisfactory improvements in its runtime infrastructure since its inception. In this article, the smart and advanced features of Windows 10 are explained. Read through the article to understand the Windows preview and utilities.

Windows 10 Crack is a software program too. The product key you get together along with your model certifies that your reproduction became now no longer obtained in violation of Microsoft’s copyright. This is the software program (KMSpic, KMSauto) used to set off Windows 10 and it’s far free. Then we will get the KMSpico software program and set off our Windows 10. This article is ready Windows 10 product keys, what they are, and the way you may effortlessly get one whilst Windows asks for it. It’s so tough that even password-cracking gear can not locate one. However, that does not suggest you haven’t any hope. There are some hints and hints for activating Windows.

Note: Before installing Windows 10, make sure your computer meets the system requirements for Windows 10. It is also recommended to visit the PC manufacturer’s website for more information on updated drivers and hardware compatibility.

Windows 10 Key Features:

  • Disk analysis, clean up unnecessary files and improve disk storage space.
  • Troubleshoot all common system troubleshooting issues.
  • Security checkups to protect your system against all vulnerabilities that may be detrimental to your operating system.
  • Startup Manager to speed up the startup process and control task manager.
  • Clean up all the jack files to use the PC in a well-organized manner.
  • Improve your system hardware as well as the software resources to fast shut down your device.
  • Its Smart Installer allows all system unwanted or malicious programs to be removed.
  • Almost, it provides registry cleaners and detectors for the Windows operating system.
  • Increase the speed of copying files or moving files from one drive or folder to another.

Windows 10 Product Keys Method File List:

Windows 10 Home EditionKeys:


Windows 10 Single Language Key:


Windows 10 Education:


Windows 10 Enterprise:

  • CKFK9-QNGF2-D34FM-99QX2-8XC4K
  • NPPR9-FWDCX-D2C8J-H872K-2YT43
  • PBHCJ-Q2NYD-2PX34-T2TD6-233PK

Windows 10 Pro Serial Key:

  • 8N67H-M3CY9-QT7C4-2TR7M-TXYCV
  • W269N-WFGWX-YVC9B-4J6C9-T83GX

Windows 10 product key: Technical Preview for Consumer:

  • 334NH-RXG76-64THK-C7CKG-D3VPT

Windows 10 product number:

  • W269N-WFGWX-YVC9B-4J6C9-T83GX

Key for Every kindof edition:


2021 product keys for Windows 10:

  • TX9XD-98N7V-6WMQ6-BX7FG-48Q99
  • TX9XD-98N7V-6WMQ6-BX7FG-H8Q99

How to Install and Use Windows 10 Crack?

  1. Download it by clicking the button below.
  2. Extract the file and start the installation.
  3. Copy the crack .exe file after extraction.
  4. When the registration is done immediately, copy and paste the cake file into the directory you installed.
  5. There you will see the option to ‘Activate Windows’.
  6. Then click Next and OK.
  7. That is, start using Windows 10 Crack.
  8. All Is Done.
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  10.  The Latest Version 2022 Free Download.

Also Download:  Resolume Arena Crack.



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