261-40-5Relevant articles and documents
Synthesis, Stereochemistry and Reactions of Selenoxanthen-10-io(alkoxalyl alkoxycarbonyl)methanides and Related Compounds
Kataoka, Tadashi,Tomimatsu, Kiminori,Shimizu, Hiroshi,Hori, Mikio
, p. 2666 - 2675 (2007/10/02)
Selenoxanthen 10-oxides (5a-d) reacted with methyl propiolate, dimethyl and diethyl acetylenedicarboxylates to afford selenoxanthen-10-iometanides (6a-i).The 9-isopropyl derivative gave only trans-ylides and the 9-phenyl congener formed cis- and trans-ylides.The stereochemistry is discussed on the basis of the nuclear magnetic resonance spectral data.Reduction of the selenoxanthenium ylides with sodium borohydride afforded the ylide lactones (16a-c) and the ylide alcohols (17a-f).The Product ratio depended on the solvent used.Keywords - selenium ylide; selenoxide; selenoxanthene; methyl propiolate; dimethyl acetylenedicarboxylate; stereoisomer; stereochemistry; sodium borohydride reduction; lactonization