185405-71-4Relevant academic research and scientific papers
Sequential pericyclic reaction of unsaturated xanthates. Intramolecular cycloaddition selectivity of the 2,4-alkadienyl 2-alkenyl sulfides
Eto, Masashi,Uemura, Toshihiro,Shimizu, Noriko,Harano, Kazunobu
, p. 13909 - 13918 (1996)
Heating of S-(1-vinyl-2-alkenyl) S-(2-alkenyl or alkynyl) dithiocarbonates (dithiolcarbonates) derived from [3,3]-sigmatropic rearrangement of O-(2,4-alkadienyl) S-(2-alkenyl or alkynyl) dithiocarbonates (xanthates) gave the 2,4-alkadienyl 2'-(alkenyl or alkynyl) sulfides, which then underwent intramolecular Diels-Alder cycloaddition to give hydrobenzo[c]thiophene derivatives. The thermal cyclization of O-(2,4-pentadienyl) derivatives of xanthate afforded mixtures of the cycloadducts, in which the cis-FUSED products slightly predominated over the trans-isomers. The selectivity of IMDA reactions is discussed based on the ab initio calculation data.
