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Topic: Kornblum DeLaMare elimination  (Read 3476 times)

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Offline dorin1993

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Kornblum DeLaMare elimination
« on: October 16, 2012, 05:20:18 PM »
Hi :)
i have a question about Kornblum DeLaMare elimination. i didn't find any mechanism of it on web, and on my book there is no mechanism, just one example...
from the example shown I realized that:
R-O-O-H + B (a base) --> R=O + BH + OH-
meaning that the base attacked the H of the C  (R-CH2-O-O-H) --> BH + R-CH=O + OH-

so:
1. is it correct? that what it is?

2. can anyone give me a link (or explanation) to the mechanism of Kornblum DeLaMare elimination?

3. i had to give the product of the reaction (Kornblum DeLaMare elimination) of the molecule that i attached picture of and a base.
so base on what i understood: R-O-O-H + B (a base) --> R=O + BH + OH-
i wrote that the product are: Cyclohexanone + BH + OH-
is it correct?
and if it is - is there a continued reaction?

thank you  :)

Offline discodermolide

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Re: Kornblum DeLaMare elimination
« Reply #1 on: October 16, 2012, 10:06:23 PM »
Development Chemists do it on Scale, Research Chemists just do it!
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Offline dorin1993

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Re: Kornblum DeLaMare elimination
« Reply #2 on: October 16, 2012, 10:11:55 PM »
i saw it. but it's Kornblum–DeLaMare rearrangement - not elimination. are they the same?

Offline BetaAmyloid

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Re: Kornblum DeLaMare elimination
« Reply #3 on: October 16, 2012, 10:15:32 PM »
In that wiki article it says that "The reaction, formally a rearrangement, ranks under the elimination reactions as already observed by the original authors."
Discovery consists of seeing what everybody has seen and thinking what nobody has thought - Albert Szent-Györgyi

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