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1,3‐Oxathiolanes from the Reaction of Aromatic and Enolized Thioketones with Monosubstituted Oxiranes by Changchun Fu; Anthony Linden; Heinz Heimgartner is a Chemistry article available to read on EtoBox.

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## Abstract The reactions of 4,4′‐dimethoxythiobenzophenone (1) with (__S__)‐2‐methyloxirane ((__S__)‐2) and (__R__)‐2‐phenyloxirane ((__R__)‐6) in the presence of a __Lewis__ acid such as BF~3~⋅Et~2~O, ZnCl~2~, or SiO~2~ in dry CH~2~Cl~2~ led to the corresponding 1 : 1 adducts, __i.e.__, 1,3‐oxathiolanes (__S__)‐3 with Me at C(5), and (__S__)‐7 and (__R__)‐8 with Ph at C(4) and C(5), respectively. A 1 : 2 adduct, 1,3,6‐dioxathiocane (4__S__,8__S__)‐4 and 1,3‐dioxolane (__S__)‐9, respectively, were formed as minor products (__Schemes 3__ and __5, Tables 1__ and __2__). Treatment of the 1 : 1 adduct (__S__)‐3 with (__S__)‐2 and BF~3~⋅Et~2~O gave the 1 : 2 adduct (4__S__,8__S__)‐4 (__Scheme 4__). In the case of the enolized thioketone 1,3‐diphenylprop‐1‐ene‐2‐thiol (10) with (__S__)‐2 and (__R__)‐6 in the presence of SiO~2~, the enesulfanyl alcohols (1′__Z__,2__S__)‐11 and (1′__E__,2__S__)‐11, and (1′__Z__,2__S__)‐13, (1′__E__,2__S__)‐13, (1′__Z__,1__R__)‐15, and (1′__E__,1__R__)‐15, respectively, as well as a 1,3‐oxathiolane (__S__)‐14 were formed (__Schemes 6__ and __8__). In the presence of HCl, the enesulfanyl alcohols (1′__Z__,2__S__)‐11, (1′__Z__,2__S__)‐13, (1′__E__,2__S__)‐13

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Author

Changchun Fu; Anthony Linden; Heinz Heimgartner

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)