کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5231828 1383739 2006 14 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Photoreactions of β-aziridinylacrylonitriles and acrylates with alkenes: the substituent effects on the formation of [3+2] cycloadducts
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Photoreactions of β-aziridinylacrylonitriles and acrylates with alkenes: the substituent effects on the formation of [3+2] cycloadducts
چکیده انگلیسی

The photochemical C,C-bond cleavage of trisubstituted aziridines 3-6 and consequent [3+2] cycloaddition with electron-deficient alkenes afforded the novel head-to-head adducts (1,2,3,5-tetrasubstituted pyrrolidines) selectively and efficiently. The aziridines 3 and 5 reacted with molecular oxygen, affording dioxazolidine 26 and cleaved products, respectively. The results may suggest that the C,C-bond of aziridine cleaves biradically. The photoreactions of N-tritylaziridines 7-9 possessing diester, dinitrile, and butadiene groups in the side chain with electron-deficient alkenes yielded 2,3-cis-pyrrolidine derivatives 29, 30, and 33 exclusively. In particular, the dinitrile 8 also reacted with non-electron-deficient alkenes. The formal synthesis of the indolizidine fragment 10 of stellettamides starting from the pyrrolidine (E)-33 was achieved in a convenient manner.

The photoreaction of tri- or disubstituted aziridines with electron-deficient alkenes afforded the novel head-to-head adducts selectivity and efficiently.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 62, Issue 47, 20 November 2006, Pages 10865-10878
نویسندگان
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