کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1314270 975957 2010 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
New fused dithiabicyclic compounds from the reaction of N,N-dialkyl perfluorothioamides with allylmagnesium halides
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
New fused dithiabicyclic compounds from the reaction of N,N-dialkyl perfluorothioamides with allylmagnesium halides
چکیده انگلیسی

Allylmagnesium reagents react with N,N-dialkylperfluorothioamide to give, at low temperature, an adduct stable enough to be trapped. At room temperature, this adduct can evolve by elimination of either a sulfide salt, leading to an iminium intermediate, and then an N,N-dialkyl-α,α-bis(allyl)-α-perfluoroalkylamine. This process is favoured if an excess of allyl magnesium is used. Alternatively, the adduct eliminates an aminyl moiety giving allyl(perfluoroalkyl)thioketone which is converted in situ into an unprecedented fused bis(perfluoroalkyl) bis(dihydrothiopyrane). A sequence deprotonation of the thioketone – oxidation of the resulting dienethiolate – dimerization of the dienethiyl radical is proposed to rationalize the formation of this unexpected bicyclic compound.

The adduct from reaction of N,N-dialkyl perfluorothioamide is stable at low temperature, then undergoes two condensation processes, one of which leading to new fused bis(dihydrothiopyrane).Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Fluorine Chemistry - Volume 131, Issue 9, September 2010, Pages 937–941
نویسندگان
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