Addition and Condensation Polymerization Processes by Gould R.F. (ed.)

By Gould R.F. (ed.)

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Tiecco described several examples of catalytic processes, in which the deselenenylation occurs with elimination. These reactions are suggested to proceed according to the general mechanism illustrated in Scheme 37 in which the reactive intermediates involved in the elimination step are not the selenoxides but the radical cations or the selenonium ions derived from the alkyl aryl selenide formed in the addition step. It has been observed that the elimination becomes greatly favored with respect to the substitution reaction whenever an electron-withdrawing group is present in the allylic position of the starting alkene so that a conjugate alkene can be obtained as the final product.

The entire process thus represents a convenient one-pot aminoselenenylation of alkenes. One of the most important addition reactions which involves nitrogen nucleophiles is the azidoselenenylation of alkenes because both the azido and the phenylseleno group can give rise to several useful transformations. These compounds were first prepared by Krief from the reaction of alkenes with PhSeBr followed by sodium azide in DMF [54]. Direct azidoselenenylation of alkenes can be effected with PhSeCl and sodium azide in DMSO [55].

In several cases, carbocyclization reactions can be more conveniently effected by independently generating the seleniranium intermediates. A simple procedure consists of the reaction of trifluoromethanesulfonic acid with b-hydroxyselenides, which can be easily obtained from the Electrophilic Selenium, Selenocyclizations 41 Scheme 31. Carbocyclizations of Dienes nucleophilic opening of epoxides with sodium phenylselenolate [107]. Kametani [108] reported that the b-hydroxyselenide 210 (Scheme 31), deriving from the epoxide of the geranyl acetate, reacts with acids to give the seleniranium intermediate 211 which then affords the cyclization product 212.

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