Thermal Rearrangements of Perchlorohexatrienes–Structures and Experimental and Theoretical Evaluation of Pathways to Isomerization and Cyclization

H Detert, D Lenoir, H Zipse

Index: Detert, Heiner; Lenoir, Dieter; Zipse, Hendrik European Journal of Organic Chemistry, 2009 , # 8 p. 1181 - 1190

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Citation Number: 7

Abstract

Abstract We have prepared trans-(1) and cis-octachloro-1, 3, 5-hexatriene (2) by known routes and studied their thermal behavior experimentally and theoretically by ab initio calculations. The three double bonds in 1 and 2 are completely decoupled due to steric hindrance by the eight Cls, as indicated by calculations as well as the single-crystal X-ray structure of 1. The cis isomer 2 can be isomerized to the trans isomer 1 by heating it to 220 ...