Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study

MB Supurgibekov, D Cantillo, CO Kappe…

Index: Supurgibekov, Murat B.; Cantillo, David; Kappe, C. Oliver; Surya Prakash; Nikolaev, Valerij A. Organic and Biomolecular Chemistry, 2014 , vol. 12, # 4 p. 682 - 689

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Citation Number: 8

Abstract

Non-fluorinated vinyldiazo compounds with trans-configuration irrespective of the nature of 3- R1-substituent (R1= H, Me, TBSO) even under ambient conditions easily cyclize to produce pyrazoles, while cis-stereoisomers undergo similar ring closure only at elevated temperatures or decompose to produce vinyloxocarbene reaction products. The 3-CF3- substituted analogues with cis-or trans-configuration do not produce pyrazoles at all, but ...