The Journal of Organic Chemistry

Thermolysis of vinyldiazomethanes as a method for the generation of vinylcarbenes and a comparison with cyclopropene photochemistry

JA Pincock, NC Mathur

Index: Pincock, James A.; Mathur, Naresh C. Journal of Organic Chemistry, 1982 , vol. 47, # 19 p. 3699 - 3706

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Citation Number: 32

Abstract

The pyrolysis of the vinyldiazomethanes 6 (X= H), 8, 9, and 10 gives mixtures of 3H- pyrazoles and cyclopropenes. The kinetics and product distribution for each case lead to a determination of the rate of vinylcarbene formation and, therefore, a direct determination of the relative carbene stabilities. The conclusion is that carbene 14 is more stable than 15. These results are then used as a basis for a discussion of the carbenes generated from ...