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Structures and Reactions of the Oxidation Products of Dimeric Ketenylidene(triphenyl)phosphorane
Author(s) -
Bestmann Hans Jürgen,
Fürst Thomas G.,
Schier Annette
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199317461
Subject(s) - oxaziridine , phosphorane , chemistry , organic chemistry , medicinal chemistry , polymer chemistry , stereochemistry
The neutral cyclobutanetrione 2 is synthesized from dimeric ketenylidene(triphenyl)phosphorane 1 by treatment with two equivalents of N‐p ‐tolylsulfonyl(phenyl)oxaziridine. Oxidation of 1 with one equivalent of the oxaziridine provides compound 3 , which like 2 was characterized by X‐ray structure analysis. Compound 3 functions as a dienophile in Diels–Alder reactions.