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Lyle McElhaney

LiAlH4 + alpha-beta unsaturated ester

Dimitra Tsiovolou  Follow
Quote from:
You have the opportunity to learn something new.

oook  ;D

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Charlie  Follow
I think LAH is a very hard nucleophile and will attac the carbonyl much faster. I should ad that for beta-nitrostyrenes 1,4-addition is faster than reduction of the nitro group so maybe you will get a mixture?

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David Southern  Follow
Quote from:
https://pubs.acs.org/doi/10.1021/ja01187a511
thanks
seems it doesn't reduce C=C....

But in another site I've found the opposite...so strange
One other thing . in the last  step when they use K2Cr2O7 on an alcohol they only get an aldehyde....I've studied that K2Cr2O7 oxidizes primary alcohol to COOH.
For Aldehyde I should need something like PCC or swern...not Cr(vi)

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Danilo Renzi  Follow
Quote from:
I think LAH is a very hard nucleophile and will attac the carbonyl much faster. I should ad that for beta-nitrostyrenes 1,4-addition is faster than reduction of the nitro group so maybe you will get a mixture?

Also RLi is a very hard nucleophile but attacks the C=O with 1,2 addition with aldehydes and ketones while for ester and amide it gives 1,4 addition (or at least a mixture) because the C=O of ester and amide is less reactive  towards a nucleohpilic attack

I wonder if  is it the same here...
I  haven't found much in the web, about the reaction of LiAlH4 with an unsaturated ester  (only found aldehydes and ketones examples)

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Cecil Williams  Follow
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Is not PCC Cr(vi)?
....right!
Sorry, I  mean K2Cr2O7  (the one used there)

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Ayesha Khan  Follow
 Is not PCC Cr(vi)?

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Brandon Lopez  Follow
You have the opportunity to learn something new.

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Betsy Poole  Follow
https://pubs.acs.org/doi/10.1021/ja01187a511

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