Journal of Organic Chemistry p. 5320 - 5328 (1988)
Update date:2022-07-31
Topics:
Snider, Barry B.
Allentoff, Alban J.
Kulkarni, Yashwant S.
Treatment of trans α,β-unsaturated acid chlorides with Et3N in benzene at reflux gives a ca. 1:1 mixture of cis and trans α,β-unsaturated ketenes in excellent yield.If there is a second double bond in the side chain, the cis isomer undergoes a type III intramolecular cycloaddition to produce a bicyclo<3.2.0>hept-3-en-6-one and/or a bicyclo<3.1.1>hept-2-en-6-one in 30-50percent yield from the acid chloride.The effect of substituents on the stereochemistry and regiochemistry of the cycloaddition is described.
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Doi:10.1021/jo00258a022
(1988)Doi:10.1002/ejoc.201800306
(2018)Doi:10.1055/s-0028-1083371
(2009)Doi:10.1002/adsc.200800307
(2008)Doi:10.1016/j.ica.2009.02.006
(2009)Doi:10.1016/S0040-4020(01)90353-9
(1988)
