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A new P‐heterocyclic family: A variety of six‐membered and bridged P‐heterocycles with 1‐benzyl substituent

A new P‐heterocyclic family: A variety of six‐membered and bridged P‐heterocycles with 1‐benzyl... The ring enlargement of 1‐benzyl‐2,5‐dihydro‐1H‐phosphole oxide (1) via the corresponding 2‐phosphabicyclo(3.1.0)hexane 2‐oxide (2) afforded, depending on the conditions, the double bond isomers (A and B) of 1,2‐dihydrophosphinine oxide 4 or that of 3‐substituted 1,2,3,6‐tetrahydrophosphinine oxides 5 and 6. Dihydrophosphinine oxides (4) were suitable starting materials for 1,2,3,4,5,6‐hexahydrophosphinine oxide 7 and 1,2,3,6‐tetrahydrophosphinine oxide 8 obtained by reductive approaches and for the double bond isomers (A and B) of 2‐phosphabicyclo(2.2.2)octadiene 2‐oxide 9 and phosphabicyclooctene oxide 10 prepared in Diels–Alder cycloaddition. Precursor 9 was utilized in the fragmentation‐related phosphorylation of alcohols. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:28–34, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20363 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

A new P‐heterocyclic family: A variety of six‐membered and bridged P‐heterocycles with 1‐benzyl substituent

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References (11)

Publisher
Wiley
Copyright
Copyright © 2008 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.20363
Publisher site
See Article on Publisher Site

Abstract

The ring enlargement of 1‐benzyl‐2,5‐dihydro‐1H‐phosphole oxide (1) via the corresponding 2‐phosphabicyclo(3.1.0)hexane 2‐oxide (2) afforded, depending on the conditions, the double bond isomers (A and B) of 1,2‐dihydrophosphinine oxide 4 or that of 3‐substituted 1,2,3,6‐tetrahydrophosphinine oxides 5 and 6. Dihydrophosphinine oxides (4) were suitable starting materials for 1,2,3,4,5,6‐hexahydrophosphinine oxide 7 and 1,2,3,6‐tetrahydrophosphinine oxide 8 obtained by reductive approaches and for the double bond isomers (A and B) of 2‐phosphabicyclo(2.2.2)octadiene 2‐oxide 9 and phosphabicyclooctene oxide 10 prepared in Diels–Alder cycloaddition. Precursor 9 was utilized in the fragmentation‐related phosphorylation of alcohols. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:28–34, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20363

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2008

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