Convenient synthesis of 1‐alkoxy‐di‐ and tetrahydrophosphinine 1‐oxides by ring enlargement

G. Keglevich, Láaszlöa Töuke, Attila Kováacs, Gáabor Töath, K. Újszászy

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The double bond of the P‐alkoxy 3,4‐dimethyl‐2,5‐dihydro‐1H‐phosphole 1‐oxides reacts easily with dichlorocarbene to give two diastereomers of an unstable adduct useful in the synthesis of ring expanded products, such as 1,2‐dihydrophosphinine oxides or 1,2,3,6‐tetrahydrophosphinine oxides. The former can be prepared by thermolysis of the adducts, while the latter are obtained by cyclopropane ring opening effected by silver nitrate in an alcoholic solvent. The preparation of the double‐bond isomers of 1‐alkoxy‐tetrahydrophosphinine oxides containing only one methyl substituent in the ring is also described. The reaction of dihydro‐1H‐phosphole oxides with dichlorocarbene can be modified to give P‐alkoxy 1,4‐dihydrophosphinine oxides in an unexpected reaction.

Original languageEnglish
Pages (from-to)61-72
Number of pages12
JournalHeteroatom Chemistry
Issue number1
Publication statusPublished - 1993


ASJC Scopus subject areas

  • Chemistry(all)

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