As a team, consider the following historic preparation of a tris(1,1-dimethylethyl) derivative of Dewar benzene, B, by

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As a team, consider the following historic preparation of a tris(1,1-dimethylethyl) derivative of Dewar benzene, B, by the photochemical isomerisation of 1,2,4-tris(1,1-dimethylethyl)benzene by van Tamelen and Pappas (1962). B does not revert to A via either a thermal or a photochemical electrocyclic mechanism. Formulate a mechanism for the conversion of A to B and explain the kinetic robustness of B with respect to the regeneration of A. 

Dewar benzene A B

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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