Stable Sulfur Ylides. XII. : Reaction of 3-Alkyl(aryl)thio-silyloxydienes Derived from Stable Sulfur Ylides with Aromatic Aldehydes. : Synthesis and Structure of Thiolanium Ylides

Jun-etsu IGARASHI; Noriyuki WATANABE; Toshio KINOSHITA; Koreharu OGATA; Sunao FURUKAWA

doi:10.1248/cpb.38.329

Jun-etsu IGARASHI, Noriyuki WATANABE, Toshio KINOSHITA, Koreharu OGATA, Sunao FURUKAWA

Author information

Keywords: methylthio-silyloxydiene, thiolanium ylide, 2, 3-dihydro-4-pyrone, titanium(IV) chloride, X-ray crystallography, Lewis acid, boron trifluoride, aromatic aldehyde

JOURNAL FREE ACCESS

1990 Volume 38 Issue 2 Pages 329-335

DOI https://doi.org/10.1248/cpb.38.329

Details

Abstract

The Lewis acid-catalyzed cyclocondensation of methylthio (or phenylthio)-silyloxydienes (2), easily derived from stable sulfur ylides (1), with several aromatic aldehydes (3) was investigated. Namely, in the case of boron trifluoride normal reaction products, 2, 3-dihydro-4-pyrones (4), were obtained in good yields. Novel reaction products, thiolanium ylides (6 and 7), were obtained in the presence of titanium(IV) chloride. The structures of 6g was established by X-ray crystallography.

Corresponding author

Register with J-STAGE for free!