Synthesis and Stereochemistry of 1H,5H-Naphtho[1,8-ef][1,3]dithiocine 2-Oxides

被引：0

作者：

P. A. Kikilo

B. I. Khairutdinov

Yu. G. Shtyrlin

V. V. Klochkov

E. N. Klimovitskii

机构：

[1] Kazan State University,Butlerov Chemical Institute

来源：

Russian Journal of Organic Chemistry | 2005年 / 41卷

关键词：

Oxygen; Organic Chemistry; Oxygen Atom; Sulfoxide; Trans Configuration;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

3-Substituted 1H,5H-naphtho[1,8-ef][1,3]dithiocines (R = H, Me, Ph, t-Bu) were oxidized with m-chloroperoxybenzoic acid to the corresponding 2-oxides having trans configuration (R ≠ H). According to the 1H and 13C NMR data (including NOESY experiments), the disubstituted compounds at room temperature exist in a boat conformation with equatorial orientation of the substituent on C3 and oxygen atom on S2. The compound with no substituent on C3 gives rise to a mixture of boat conformers with axial and equatorial sulfoxide oxygen atoms at a ratio of 83:17.

引用

页码：1089 / 1092

页数：3

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