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

✍ Scribed by Gyöurgy Keglevich; Láaszlöa Töuke; Attila Kováacs; Gáabor Töath; Kálmán Újszászy

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
850 KB
Volume
4
Category
Article
ISSN
1042-7163

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✦ Synopsis

The double bond of the P-alkoxy 3,4-dimethyl-2,5dihydro-1 H-phosphole I -oxides reacts easily with dichlorocarbene to give two diastereomers of an unstable adduct useful in the synthesis of ring expanded products, such as I ,2-dihydrophosphinine oxides or I ,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 I-alkoxytetrahydrophosphinine oxides containing only one methyl substituent in the ring is also described. The reaction of dihydro-1 H-phosphole oxides with dichlorocarbene CaiY be modified to give P-alkoxy I ,4dihydrophosphinine oxides in a n unexpected reaction.

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