کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5273838 | 1385499 | 2012 | 4 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
A new approach to the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans by the 1,5-CH insertion reaction of magnesium carbenoids
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی آلی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
1-Alkoxy-1-[2-chloro-2-(p-tolylsulfinyl)ethyl]cycloalkanes were prepared from various cyclic ketones in good overall yields. Treatment of these cycloalkanes bearing a sulfinyl group with i-PrMgCl resulted in the formation of 1-oxaspiro[4.n]alkanes in high to quantitative yields via the 1,5-CH insertion reaction of generated magnesium carbenoid intermediates. When this procedure was commenced with acyclic ketones, multi-substituted tetrahydrofurans were obtained in up to a 96% yield. This procedure provides a new and good way for the synthesis of 1-oxaspiro[4.n]alkanes and tetrahydrofurans with the formation of a carbon-carbon bond between a carbenoid carbon and a non-activated carbon in high yields. The oxygen atom in the magnesium carbenoid intermediates was proved to act very important roles in the 1,5-CH insertion reaction.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 53, Issue 16, 18 April 2012, Pages 2074-2077
Journal: Tetrahedron Letters - Volume 53, Issue 16, 18 April 2012, Pages 2074-2077
نویسندگان
Tsuyoshi Satoh, Tsukasa Yasoshima, Hitoshi Momochi,