N. Satyamurthy, K. Berlin, M. Hossain
Feb 1, 1984
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Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract The synthesis of several 1-oxa-6-heteraspiro[2.5]octanes is reported herein for the first time. Stereochemical analysis via NMR studies and a single crystal X-ray diffraction analysis of 6-phenyl-1-oxa-6-phosphaspiro[2.5]octane 6-sulfide have been completed and provide the basis for correlations of structures for other members of the families yet unknown. Epoxidation of cis-2,6-diphenyl-4-thianone with dimethyl-oxosulfonium methylide in DMSO led, surprisingly, to a tertiary alcohol, presumably via ring opening of the expected intermediate epoxide. This is the first example of this type of ring opening in the presence of this base but the reaction time was longer than that normally employed in this process. Since the family members of the parent spiro[2.5]octanes are rare, an X-ray diffraction analysis was performed on 6-phenyl-1-oxa-6-phosphaspiro[2.5]octane 6-sulfide. This analysis revealed a space group of Pna21 with cell dimensions of: a=13.056(3) A, b=14.268(3) A, and c=6.1522(11) A. The phos...