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Synthesis of dimeric 1,3,2λ5‐benzoxazaphospholes from phosphinic acid derivatives by silylation/desiloxylation

Synthesis of dimeric 1,3,2λ5‐benzoxazaphospholes from phosphinic acid derivatives by... The reaction of N,N,O‐tris(trimethylsilyl)‐o‐aminophenol with two equivalents of phosphinic chloride yielded dimeric 2,2‐disubstituted 1,3,2λ5‐benzoxazaphospholes and trimethylsilyl phosphinate. The chlorides having the bulk substituents (o‐chlorophenyl or tert‐butyl) at phosphorus or containing PN and PO bonds (instead of a PC bond) either didn't react at all or reacted to retain the phosphoryl group. Being stable in solution at 20°C, the individual diastereoisomers of dimeric 1,3,2‐benzoxazaphospholes were converted upon warming to an equilibrium mixture of isomers. When reacted with another dimer each gave a mixed dimeric compound having two different phosphorus atoms in the molecule. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Synthesis of dimeric 1,3,2λ5‐benzoxazaphospholes from phosphinic acid derivatives by silylation/desiloxylation

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References (2)

Publisher
Wiley
Copyright
Copyright © 1990 Wiley Subscription Services
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.520010610
Publisher site
See Article on Publisher Site

Abstract

The reaction of N,N,O‐tris(trimethylsilyl)‐o‐aminophenol with two equivalents of phosphinic chloride yielded dimeric 2,2‐disubstituted 1,3,2λ5‐benzoxazaphospholes and trimethylsilyl phosphinate. The chlorides having the bulk substituents (o‐chlorophenyl or tert‐butyl) at phosphorus or containing PN and PO bonds (instead of a PC bond) either didn't react at all or reacted to retain the phosphoryl group. Being stable in solution at 20°C, the individual diastereoisomers of dimeric 1,3,2‐benzoxazaphospholes were converted upon warming to an equilibrium mixture of isomers. When reacted with another dimer each gave a mixed dimeric compound having two different phosphorus atoms in the molecule.

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 1990

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