930-29-0Relevant articles and documents
Facile generation of a strained cyclic vinyl cation by thermal solvolysis of cyclopent-1-enyl-λ3-bromanes
Miyamoto, Kazunori,Shiro, Motoo,Ochiai, Masahito
supporting information; experimental part, p. 8931 - 8934 (2010/02/28)
Last of the cyclic vinyl cations: The simple solvolysis of cyclopent-1 -enyl-13-bromane efficiently generates the highly strained cyclopent-1 -enyl cation at room temperature (see scheme). The very high nucleofugality of the aryl-13-bromanyl groups are re
Photochemistry of Alkyl Halides. 10. Vinyl Halides and Vinylidene Dihalides
Kropp, Paul J.,McNeely, Steven A.,Davis, Robert Drummond
, p. 6907 - 6915 (2007/10/02)
The photobehavior of the acyclic vinyl iodide 2, the 1-iodocycloalkenes 11-14 and 39, the (halomethylene)cycloalkanes 45-48, and the (dihalomethylene)cyclohexanes 62-64 has been studied.Except for the dichloride 64, which exhibited only radical behavior, each of the halides afforded a mixture of ionic and radical products.The two bromides studied, 48 and 63, afforded lower ratios of ionic to radical products than the corresponding iodides 45 and 62.Irradiation of vinyl iodides was found to be a convenient and powerful method for the generation of vinyl cations, including the highly strained 1-cyclohexenyl and 1-cyclopentenyl cations and the unstabilized α-unsubstituted cations 51 and 54.The latter cations underwent rearrangement to the ring-expanded 1-cycloalkenyl cations 28 and 36, respectively.Lowering the temperature of the irradiation of iodides 13, 14, and 45 resulted in an increased ratio of ionic to radical products.However, iodide 47, which underwent principally fragmentation to enyne 61, showed little temperature effect.