136547-75-6Relevant academic research and scientific papers
[3,3]Sigmatropic ring expansion of cyclic thionocarbonates. IV. Relationship between ring size of cyclic thionocarbonates and geometry of created double bond in medium- and large-membered thiolcarbonate
Harusawa,Osaki,Kurokawa,Fujii,Yoneda,Kurihara
, p. 1659 - 1667 (2007/10/02)
Medium- and large-membered cyclic thiolcarbonates containing an (E)- or (Z)-double bond were synthesized by two methods using [3,3]sigmatropic ring expansion of cyclic thionocarbonates. The [3,3]sigmatropic ring expansion proceeds exclusively via the transition state bearing the chain tethered in a cis relationship when the cyclic thionocarbonates are 8-membered or smaller. Importantly, the ring of the cyclic thionocarbonates determines the double bond geometry of the thiolcarbonate. Conversion of the cyclic thiolcarbonates into (E)- or (Z)-allylic sulfides is also described.
