叠氮化钠处理 1,6,10,14-四氧杂螺[2.1.25.1.29.1.213.13]十六烷时的立体依赖性亲核开环反应

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-08-31 DOI:10.1007/s11172-024-4330-7

K. N. Sedenkova, D. V. Savchenkova, O. V. Ryzhikova, Yu. K. Grishin, E. B. Averina

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引用次数: 0

摘要

在叠氮化钠的作用下，研究了 1,6,10,14-四氧杂四环螺[2.1.25.1.29.1.213.13]十六烷（一种环辛烷结构，螺与四个环氧乙烷片段融合）的亲核开环反应。根据起始化合物中立体中心的相对构型，反应以分子内跨annular 环化方式进行，形成 9-oxabicyclo[3.3.1]nonane 骨架，或以环氧乙烷环的独立亲核开环方式进行，生成环辛烷系列的四氮唑四醇。

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Stereo-dependent nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane upon treatment with sodium azide

Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.2⁵.1.2⁹.1.2¹³.1³]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series.

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.