Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins

A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. So...

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Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2002-01, Vol.177 (1), p.251-259
Main Authors: Nifantiev, Eduard E., Khrebtova, Svetlana B., Kulikova, Yulia V., Predvoditelv, Dmitrii A., Kukhareva, Tat′yana S., Petrovskii, Pavel V., Rose, Mirjam, Meier, Chris
Format: Article
Language:English
Subjects:
2-hydroxybenzylic Alcohol
Arbuzov-Michaelis-type Isomerization
Benzodioxaphosphorins
Benzooxaphosphole Oxides
Cyclosaligenyl Nucleotides
Saligenin
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Summary:A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to th P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500210234