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Reactivity of diacyloxyiodobenzenes toward trivalent phosphorus nucleophiles

✍ Scribed by Sławomir Makowiec; Janusz Rachon

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
144 KB
Volume
14
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

The reaction of diacyloxyiodobenzenes and tetravalent phosphorus nucleophiles was investigated. It was established that both H‐phosphonates and secondary phosphine oxides react with diacetoxyiodobenzene in alcohols in the presence of sodium alcoholates yielding trialkyl phosphates and alkyl phosphinates respectively. For this transformation reactive intermediate 6 is proposed. In contrast to this, the treatment of diacetoxyiodobenzene with 3 equiv of sodium diisopropyl phosphite in THF produces diisopropyl 1‐(diisopropoxyphosphinyl)ethylphosphonate with excellent yield. It was found that diacyloxyiodobenzene/PR~3~ system may serve as an acylating agent; the acylation process can proceed via carboxylic acid anhydride or acylphosphonium salt 17 depending on the protocol used. New very efficient method for synthesis of 2,4,6‐trimethylbenzoic anhydride was developed. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:352–359, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10161

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