Cycloexpansion Reactions in Benzo[e]-1,3,2-diheterophosphorin-4-ones and 4-Oxo-1,3,2-dioxaphospholanes

Abstract

The peculiarities of the reactions of 2-R-benzo[d]-1,3,2-dioxaphosphorin-4-ones, 2-R-naphtho[d]-1,3,2-dioxaphosphorin-4-ones, 2-R-8-azabenzo[e]-1,3,2-dioxaphosphorin-4-ones, and 2-R-1,3,2-dioxaphospholan-4-ones with unsaturated compounds are summarized in the review. The reactions proceed in the mild conditions and lead to the formation of the seven- and six-membered heterocycles 1,3,2-dioxa-, 1,3,2-oxaza-, 1,4,2-dioxa-, and 1,4,2-oxazaphosphepines and 1,3,2- and 1,4,2-dioxaphosphorinanes with a high regio- and stereoselectivity. The hydrolysis and thermolysis of the some benzophosphepine derivatives leads to the substituted fluorinated ketones and various nonphosphorus heterocycles.

Keywords:

• Benzodioxaphosphorine
• benzooxazaphosphorine
• chloral
• dihydroxyterephthalic acid
• dioxaphospholane
• dioxaphosphepine
• dioxaphosphorinane
• hexafluoroacetone
• hydroxy-nicotinic acid
• hydroxypicolinic acid
• mandelic acid
• oxazaphosphepine
• pamoic acid
• phosphonate
• salicylic acid

Acknowledgments

The work was financially supported by Russian Foundation for Basic Research (project No. 10-03-00525).