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Fragmentation-related phosphinylations using 2-aryl-2-phosphabicyclo[2.2.2]oct- 5-ene- and -octa-5,7-diene 2-oxides

✍ Scribed by György Keglevich; Helga Szelke; Ágnes Bálint; Tímea Imre; Krisztina Ludányi; Zoltán Nagy; Miklós Hanusz; Kálmán Simon; Veronika Harmat; László Tőke

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

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✦ Synopsis

Abstract

A series of new P‐methylphenyl P‐heterocycles are introduced. The para and ortho substituted 2,5‐dihydro‐1H‐phosphole oxides (1a and 1b) were converted to the double‐bond isomers (A and B) of 1,2‐dihydrophosphinine oxides (3a and 3b) via the corresponding phosphabicyclo[3.1.0]hexane oxides (2a or 2b). Isomeric mixture (A and B) of the dihydrophosphinine oxides (3a and 3b) gave, in turn, the isomers (A and B) of phosphabicyclo[2.2.2]oct‐5‐enes (4a and 4b) or a phosphabicyclo[2.2.2]octa‐5,7‐diene (5) in Diels‐Alder reaction with dienophiles. The bridged P‐heterocycles (4 and 5) were useful in the photo‐ or thermoinduced fragmentation‐related phosphinylation of hydroxy compounds and amines. The new precursors (4a and 4b) were applied in mechanistic investigations. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:443–451, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10176

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A 2-phosphabicyclo[2.2.2]oct-7-ene oxide (2) and a 2-phosphabicyclo[2.2.2]octa-5,7-diene oxide (3) with ethyl substituent on the phosphorus atom was synthesized and their fragmentation properties were studied. The phosphabicyclooctadiene oxide (3) could be utilized in both the UV light-mediated phos