The Journal of Organic Chemistry

Bimanes. 15. Kinetics and mechanism of the hydroxide ion reaction with 1, 5-diazabicyclo [3.3. 0] octadienediones (9, 10-dioxabimanes)

H Kanety, EM Kosower

Index: Kanety, Hannah; Kosower, Edward M. Journal of Organic Chemistry, 1982 , vol. 47, # 22 p. 4222 - 4226

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Citation Number: 5

Abstract

The rate constants for the reaction of hydroxide ion with syn-and anti-9, lO-dioxabimanes (1, 5-diazabicy-clo [3.3. 0] octadienediones) correlate with the function [u (R,)+ 0.5~(R'')], p value of 3.0 (R,= CH, or H), and with [u (R,)+ 0.50 (Rill, p value of ca. 4 (R,= C1 or H). The p value for hydrolysis of lactones produced by photoisomerization of anti-bimanes is 3.7. Structures of the ring-opened hydrolysis products as l (2)-pyrazolinonylacrylic acids have ...

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