1??[(E)??2??Arylethenyl]??2, 2??diphenylcyclopropanes: Kinetics and Mechanism of Rearrangement to Cyclopentenes

…, R Huisgen, V Arion, R Sustmann

Index: Mulzer, Johann; Huisgen, Rolf; Arion, Vladimir; Sustmann, Reiner Helvetica Chimica Acta, 2011 , vol. 94, # 8 p. 1359 - 1388

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Citation Number: 7

Abstract

Abstract Kinetic measurements for the thermal rearrangement of 2, 2-diphenyl-1-[(E)-styryl] cyclopropane (22a) to 3, 4, 4-triphenylcyclopent-1-ene (23a) in decalin furnished ΔH equation image= 31.0±1.2 kcal mol− 1 and ΔS equation image=− 6.0±2.6 eu The lowering of ΔH≠ by 20 kcal mol− 1, compared with the rearrangement of the vinylcyclopropane parent, is ascribed to the stabilization of a transition structure (TS) with allylic diradical ...

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