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2‐Chloro‐2 H ‐phosphirene/1‐Chloro‐1 H ‐phosphirene Isomerization by [1,3]‐Chlorine Shift
Author(s) -
Wagner Oliver,
Ehle Michael,
Regitz Manfred
Publication year - 1989
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.198902251
Subject(s) - isomerization , antiaromaticity , chemistry , carbene , phosphorus , nitrogen , chlorine , nucleophile , planarity testing , medicinal chemistry , photochemistry , organic chemistry , crystallography , molecule , aromaticity , catalysis
The contrasting behavior of nitrogen and phosphorus is shown by the product of reaction (a). Whereas only the 2 H isomers of azirines are known to be stable, the initial 2 H products of this thermally induced carbene addition undergo [1,3] chlorine shift to afford the 1 H isomers 1 . The stability of 1 might be due to a decrease in its potentially antiaromatic character by non‐planarity at phosphorus. Nucleophilic substitutions provide a large variety of functionalized phosphirenes from 1 .