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Preparation of 1,3-diphosphabuta-1,3-dienes from sterically encumbered phosphaalkyne and phosphaethenyllithium

✍ Scribed by Shigekazu Ito; Hideaki Miyake; Hiroki Sugiyama; Masaaki Yoshifuji

Book ID
102229012
Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
107 KB
Volume
16
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Kinetically stabilized 2‐lithio‐1‐(2,4,6‐tri‐t‐butylphenyl)‐1‐phosphapropene was allowed to react with a bulky phosphaalkyne Mes*CP (Mes* = 2,4,6‐t‐Bu~3~C~6~H~2~) followed by quenching with iodomethane or benzyl bromide to give the corresponding 1,3‐diphosphabuta‐1,3‐dienes. The presence of the bulky Mes* group on the 1‐phosphorus atom prevents intramolecular [2+2] cyclization and gave the PCPC skeleton, whereas Mes*CP reacted with half an equivalent of nucleophile to afford the PCPC four‐membered ring compounds. X‐ray crystallography of 4‐benzyl‐1,3‐diphosphabuta‐1,3‐diene confirmed the molecular structure showing conjugation on the 1,3‐diphosphabuta‐1,3‐diene moiety. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:357–360, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20104

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