SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF 2-ARYLSELENO-1,3-DITHIANES - CRYSTAL AND MOLECULAR-STRUCTURE OF 2-(4-METHOXYPHENYLSELENO)-1,3-DITHIANE AND 2-(4-TRIFLUOROMETHYLPHENYLSELENO)-1,3-DITHIANE

被引：15

作者：

PINTO, BM ^{[1
]}

SANDOVALRAMIREZ, J ^{[1
]}

SHARMA, RD ^{[1
]}

WILLIS, AC ^{[1
]}

EINSTEIN, FWB ^{[1
]}

机构：

[1] SIMON FRASER UNIV,DEPT CHEM,BURNABY V5A 1S6,BC,CANADA

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1986年 / 64卷 / 04期

关键词：

Conformations - X ray crystallography;

D O I：

10.1139/v86-118

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 2-(4-methoxyphenylseleno)-l,3-dithiane 3 and 2-(4-trifluoromethylphenylseleno)-l,3-dithiane 5 from 2-chloro-l,3-dithiane 1 and the corresponding sodium arylselenolates is described. Nuclear magnetic resonance spectroscopic investigation of the products indicates that the compounds exist predominantly in a conformation in which the arylseleno moiety adopts an axial orientation. X-ray crystallographic investigation indicates that the 1,3-dithiane ring exists in the chair conformation with the arylseleno moiety in the axial orientation. Compound 3 is orthorhombic, space group P212121 with a = 5.449(2) A, b = 9.217(2) A, c = 24.860(3) A V = 1248.5 A3, Z = 4. The structure was refined to R = 0.038 for 689 reflections with / > 2.3σ(/). Compound 5 is monoclinic, space group C2/c, with a = 28.628(7) A, b = 5.246(2) A, c = 21.342(5) A, β = 121.12(1)°, V = 2743.8 A3, Z = 8. Its structure refined to R = 0.064 for 966 reflections with / > 2.3σ (/).

引用

页码：732 / 738

页数：7

共 64 条

[1] CONFORMATION AND ANOMERIC EFFECT IN 2-HALOTETRAHYDROPYRANS [J].