1978•Journal of the Chemical Society Chemical CommunicationsRequires access
The thermal rearrangements of pentadienylammonium ylides. Competing [1,2], [3,2], and [5,2] rearrangements
Kan Chantrapromma, W. David Ollis, Ian O. Sutherland
Open publisher page 0 citations
Abstract
The pentadienylammonium ylides (9) rearrange thermally to give the products (14), (15), (16), and (17) by two distinct reaction pathways; the first is formally a forbidden sigmatropic rearrangement and it involves an interacting radical pair having some translational freedom giving predominantly the products of [1,2] and [5,2] rearrangements, and the second is formally an allowed [3,2] sigmatropic rearrangement which involves an interacting radical pair indistinguishable from the transition state of a concerted pericyclic process.