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The synthesis of alkenes via epi-phosphonium species: 2. A phosphorus Ramberg-Bäcklund reaction

✍ Scribed by Nicholas J. Lawrence; Faiz Muhammad

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
716 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Stilbene may be synthesised with Z-selectivity from (~-bromobenzyl)benzyldiphenylphosphonium bromide by the action of amine bases. A series of stilbeues was synthesised by the action of N-bromosuecinimide and 2,2,6,6-tetramethyipiperidine directly upon dibenzyldiphenylphosphonium salts. The reaction, essentially a phosphonium analogue of the Ramberg-B~cklund displays cis selectivity. The dibenzyldiphenylphosphonium salts were prepared by the one pot polymethylhydrosfloxane/titanium(IV) isopropoxide mediated reduction/alkylation of benzyldiphenyiphosphine oxides.

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