116565-31-2Relevant academic research and scientific papers
Type III Intramolecular Cycloadditions of Vinylketenes
Snider, Barry B.,Allentoff, Alban J.,Kulkarni, Yashwant S.
, p. 5320 - 5328 (1988)
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 bicyclohept-3-en-6-one and/or a bicyclohept-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.
