کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5286162 | 1385775 | 2007 | 6 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
A highly stereoselective transformation of carboxylic esters to trisubstituted olefins via cationic cyclopropyl-allyl rearrangement of sulfonates of cis-1,2-disubstituted cyclopropanols
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
Methanesulfonates of readily available cis-1,2-disubstituted cyclopropanols on reaction with magnesium bromide in diethyl ether undergo cyclopropyl-allyl rearrangement to afford allyl bromides, with an (E)-trisubstituted double bond, as main products. The amount of the corresponding (Z)-isomers did not exceed 5% when the reaction was performed at 0 °C, and the major concomitant products were the regioisomeric secondary bromides. The latter are sufficiently less reactive towards sulfur, phosphorus and hydrogen nucleophiles than the dominant (E)-disubstituted allyl bromides and these reactions are suitable for the stereoselective preparation of trisubstituted olefins.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 48, Issue 48, 26 November 2007, Pages 8424-8429
Journal: Tetrahedron Letters - Volume 48, Issue 48, 26 November 2007, Pages 8424-8429
نویسندگان
Dzmitry G. Kananovich, Alaksiej L. Hurski, Oleg G. Kulinkovich,