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An unusual synthesis of 2,3‐dihydrophosphindole 1‐oxides
Author(s) -
Hughes Alan N.,
Phisithkul Siriporn,
Rukachaisirikul Thitima
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160725
Subject(s) - phosphole , chemistry , pyrolytic carbon , oxide , stereospecificity , hydrogen , phosphorus , phosphide , decomposition , inorganic chemistry , organic chemistry , pyrolysis , catalysis
A very simple route to dimeric phosphole oxides is reported as is the pyrolytic decomposition of these phosphorus‐bridged dimers. Like similar dimeric phosphole sulfides, these phosphole oxide dimers readily eliminate the bridging phosphorus grouping upon strong heating but, unlike the analogous sulfides, hydrogen transfer to give a 2,3‐dihydrophosphindole 1‐oxide rather than hydrogen elimination to give the fully unsaturated phosphindole oxide occurs. This hydrogen transfer is shown to be non‐stereospecific and some mechanistic implications of this are briefly discussed.