Computational studies and qualitative analysis of the orbitals have suggested that the pentadienyl alcohol systems can undergo a [3, 3]- and [3, 5]-sigmatropic rearrangement. Based on orbital analysis the rearrangement is predicted to go via an unusual pseudopericyclic transition state. Conformationally constrained alcohol derivatives (acetates, xanthates and imidates) were designed and synthesized. Thermolysis yielded a range of products and the mechanistic details for the formation of these will be discussed. 

Study of [3, 3]- and [3, 5]-sigmatropic rearrangements of pentadienyl alcohol derivatives

246th National Meeting (2013)

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