85891-62-9Relevant academic research and scientific papers
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
STABLE SELENOXANTHENIUM YLIDES : SYNTHESIS AND NEW REDUCTIVE CYCLIZATION OF SELENOXANTHEN-10-IO(ALKOXALYL ALKOXYCARBONYL)METHANIDES AND THEIR RELATED COMPOUNDS
Kataoka, Tadashi,Tomimatsu, Kiminori,Shimizu, Hiroshi,Hori, Mikio
, p. 75 - 78 (2007/10/02)
Stereoisomers of 9-substituted selenoxanthen-10-io(alkoxalyl alkoxycarbonyl)methanides were prepared from the corresponding selenoxides and activated acetylenes.In the reaction of 9-phenylselenoxanthene 10-oxide(1c) with methyl propiolate afforded an unexpected product, methyl 9-phenylselenoxanthen-9-ylpropiolate(5) together with ylide(2e).The selenonium ylides underwent new reductive cyclization with sodium borohydride to afford new cyclic selenonium ylides.
