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Friday, July 08, 2005

Addition of Grignard Reagents to Ketones


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This is an example of the reaction of a ketone with a Grignard reagent, which gives a tertiary alcohol. The paper presents a study of several different idol-3-ones reacting with Grignard reagents. Idol-3-ones are potentially useful intermediates in the synthesis of alkaloids and pharmaceutical agents.
Going one step further: due to the lack of stability in the tertiary alcohol, a rearrangement is observed on the alcohol molecule, creating a gain in resonance stabilization in the final molecule. The study examined a variety of conditions under which the rearrangement occurred, in order to recognize the most efficient one. It was determined that the rearrangement took place with great facility under acidic or basic conditions or was thermally induced.

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4 Comments:

  • I'm not sure how to make the article available for everyone!?

    By Blogger Petia, at 4:28 PM  

  • Anyone on the Drexel Campus (or any university with a subscription to the journal) will have access. If you are not on campus but are running VPN you will also have access. For those who don't have access to the full text at least they will see the abstract in CiteULike, which you must use for full marks.

    By Blogger Jean-Claude Bradley, at 4:37 PM  

  • It worked !!

    By Blogger Petia, at 8:37 PM  

  • 8/10 marks
    1) Your CiteULike link does not have a link to the online version of the article
    2) Some of your benzene rings are missing double bond

    This is an interesting example of a 1,2 shift mediated by a N to O stabilized carbocation.

    By Blogger Jean-Claude Bradley, at 7:16 AM  

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