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Allylic Rearrangements. XXI. Further Studies Related to the Nature of the Butenyl Grignard Reagent

Young, William G. and Roberts, John D. (1946) Allylic Rearrangements. XXI. Further Studies Related to the Nature of the Butenyl Grignard Reagent. Journal of the American Chemical Society, 68 (8). pp. 1472-1475. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20150930-135821906

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Abstract

Cleavage of the butenyl Grignard reagent by water gives a mixture of butenes, although the products from a variety of addition and coupling reactions are almost exclusively α-methylallyl derivatives. To gain further information regarding the butenyl Grignard reagent we have turned to the study of some reactions expected to cleave the reagent to butenes through the operation of mechanisms different from that involved with water. For the cleavage of butenylmagnesium bromide by an enolizable ketone, acetomesitylene was chosen since several investigators have shown that organometallic compounds such as ethylmagnesium bromide, n-butyllithium and phenylsodium do not add to the carbonyl group of this compound but give enolization products exclusively. Contrary to expectation, the reaction of butenylmagnesium bromide with acetomesitylene gave a negligible amount of enolization products (less than 3% of the calculated amount of butenes was detected). From the reaction mixture was recovered about 12% of the original ketone and the principal product was the tertiary alcohol, α-methylallylmesitylmethylcarbinol (I). The yield was 83%.


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http://dx.doi.org/10.1021/ja01212a024DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja01212a024PublisherArticle
Additional Information:© 1946 American Chemical Society. Received October 16, 1945. Presented in part before the Division of Organic Chemistry of the American Chemical Society at New York City, September, 1944. [John D. Roberts] Abbott Laboratories Research Fellow, 1943-1944.
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Record Number:CaltechAUTHORS:20150930-135821906
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20150930-135821906
Official Citation:Allylic Rearrangements. XXI. Further Studies Related to the Nature of the Butenyl Grignard Reagent William G. Young and John D. Roberts Journal of the American Chemical Society 1946 68 (8), 1472-1475 DOI: 10.1021/ja01212a024
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:60627
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:05 Oct 2015 17:34
Last Modified:05 Oct 2015 17:34

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