Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis
Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.
Maeta, Naoya,Kamiya, Hidehiro,Okada, Yohei
supporting information
p. 6551 - 6566
(2020/07/14)
Reactions of Olefins with Compounds Containing a Vinyl or Vinylidene Group over Aluminosilicate Catalysts
Reactions of camphene and styrene with α,β-unsaturated carbonyl compounds and also of styrene with dipentene and γ-terpinene on aluminosilicate catalysts yield, depending on the nature of compound containing the vinyl group, either and cyclization products or products of formal substitution of the vinyl hydrogen atom in the olefin.Reaction of camphene with formaldehyde yields tricyclic ethers, instead of usual products of Prins reaction.
Tatarova, L. E.,Yarovaya, O. I.,Volcho, K. P.,Korchagina, D. V.,Salakhutdinov, N. F.,et al.
p. 908 - 920
(2007/10/03)
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