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Preparation, structure, and reactivity of a new heterocyclic system-1-thio-2,8-diphenyl-2,5,8-triaza-1λ5-phosphabicyclo[3.3.0]octane

✍ Scribed by Susan Laurens; Vimal V. H. Ichharam; Tomasz A. Modro

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
117 KB
Volume
12
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

A new heterocyclic system, 1‐thio‐2,8‐diphenyl‐2,5,8‐triaza‐1λ^5^‐phosphabicyclo[3.3.0]octane, has been prepared, and its structure was confirmed by single‐crystal X‐ray diffraction. Preliminary reactivity studies demonstrated a complex mechanism for the acid‐catalyzed methanolysis. Gas chromatography–mass spectrometry analysis indicates a reversible substitution leading to the monocyclic, eight‐membered product, followed by two rearrangement reactions: isomerization to the 1,3,2‐diazaphosphorinane derivative, and to the SMe thioester via the oxygen → sulfur migration of the methyl group. © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:327–332, 2001

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