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Synthesis, Structure, and Thermolysis of an Unusual Azaphosphasiliridine
Author(s) -
Driess Matthias,
Pritzkow Hans
Publication year - 1992
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.199207511
Subject(s) - nitrene , thermal decomposition , diazomethane , chemistry , cycloaddition , decomposition , stereochemistry , medicinal chemistry , organic chemistry , catalysis
A π complex of a phosphasilene with the nitrene form of diphenyldiazomethane is the formal description of the azaphosphasiliridine 1 suggested by the X‐ray structure analysis. Compound 1 is the first product of the [2 + 1] cycloaddition of a diazomethane to a (p–p) π bond of heavy main‐group elements whose structure could be completely characterized. Despite its bulky substituents, 1 rearranges by a thermal elimination of N 2 , in which 2 and 3 are intermediates. Surprisingly, it is not the phosphasilirane 3 , but the isomer 4 that is the final product of the thermolysis. Is = 2,4,6‐ i Pr 3 C 6 H 2