Substituent effects on rates of formation of methoxy-substituted carbonyl ylides from 2-aryl-2-methoxy-and 5-aryl-2-methoxy-Δ3-1, 3, 4-oxadiazolines

…, PJ Smith, J Warkentin

Index: Bekhazi, Michel; Smith, Peter J.; Warkentin, John Canadian Journal of Chemistry, 1984 , vol. 62, p. 1646 - 1652

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Citation Number: 22

Abstract

2-Aryl-2-methoxy-5, 5-dimethyl-Δ3-1, 3, 4-oxadiazolines (4) and 5-aryl-2-methoxy-2, 5- dimethyl-Δ3-1, 3, 4-oxadiazolines (5) were synthesized. Compounds 4 decompose in solution with first order kinetics. Rate constants are correlated with Hammett substituent constants (σ-) with ρ (49.2° C)= 0.74 and 0.89 for CCl4, and CD3OD, respectively. The final products from 4 indicate that thermolysis involves the cleavage of both CN bonds, to form ...

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