Stereochemical aspects of ether oxygen participation. VI. Acid-promoted reactions of medium-sized cis [n. 1.0] oxabicyclics

LA Paquette, MK Scott

Index: Paquette,L.A.; Scott,M.K. Journal of the American Chemical Society, 1972 , vol. 94, p. 6751 - 6759

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Citation Number: 20

Abstract

Abstract: The solvolysis of cis-3-oxabicyclo [5.1. O] octane (1) gave a mixture of three diformates (14, 15, and 16) which are the result of C2-Ca bond heterolysis of the protonated ether. For comparison purposes, 15 was synthesized unequivocally while 14 and 16 were converted to their dihydro derivatives. Suitable credence to the mechanism proposed above was gained by submitting diol 43 to the formolysis conditions. All three formates were ...