Reactions of silica chloride (SiO2Cl)/DMSO, a heterogeneous system for the facile regeneration of carbonyl compounds from thioacetals and ring-expansion annelation of cyclic thioacetals

被引:57
作者
Firouzabadi, H [1 ]
Iranpoor, N [1 ]
Hazarkhani, H [1 ]
Karimi, B [1 ]
机构
[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran
关键词
D O I
10.1021/jo016343c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silica chloride (SiO2Cl)/DMSO, as a heterogeneous system, has been efficiently used for deprotection of thioacetals into aldehydes in dry CH2Cl2 at room temperature. Thioketals without enolizable hydrogens adjacent to a sulfur atom are converted easily to the corresponding ketones in high yields under similar reaction conditions. However, thioketals with enolizable methyl and methylene groups undergo ring-expansion reactions to afford 1,4-dithiepins and 1,4-dithiins in dry CH2Cl2 at room temperature in good yields.
引用
收藏
页码:2572 / 2576
页数:5
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