2‐Chloro‐2 H ‐phosphirene/1‐Chloro‐1 H ‐phosphirene Isomerization by [1,3]‐Chlorine Shift | Zendy

Wagner Oliver | Zendy; Ehle Michael | Zendy; Regitz Manfred | Zendy

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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 .

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