SYNTHESIS OF 3-ARYL-1,4-BENZOXATHIANES - APPLICATION TO THE PREPARATION OF A SWEET COMPOUND

被引：22

作者：

ARNOLDI, A ^{[1
]}

BASSOLI, A ^{[1
]}

CAPUTO, R ^{[1
]}

MERLINI, L ^{[1
]}

PALUMBO, G ^{[1
]}

PEDATELLA, S ^{[1
]}

机构：

[1] UNIV NAPLES,DIPARTIMENTO CHIM ORGAN & BIOL,I-80134 NAPLES,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 09期

关键词：

D O I：

10.1039/p19940001241

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Attempts to prepare 3-phenyl-1,4-benzoxathiane by acid-catalysed ring-closure of 2-(2-hydroxyphenylthio)-2-phenylethanol gave instead 2-phenyl-1,4-benzoxathiane, via a rearrangement probably involving an episulfonium ion. The first synthesis of 3-aryl-1,4-benzoxathianes was obtained by N-bromosuccinimide-promoted oxidative rearrangement of 1,3-oxathiolanes derived from cyclohexanone. The application of this route to the synthesis of 3-(3-hydroxy-4-methoxyphenyl)-1,4-benzoxathiane, a compound ca. 2000 times as sweet as sucrose, is reported.

引用

页码：1241 / 1244

页数：4

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