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.

Synthesis of 3-aryl-1,4-benzoxathianes: application to the preparation of a sweet compound / A. Arnoldi, A. Bassoli, R. Caputo, L. Merlini, G. Palumbo, S. Pedatella. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 9:9(1994), pp. 1241-1244.

Synthesis of 3-aryl-1,4-benzoxathianes: application to the preparation of a sweet compound

A. Arnoldi
Primo
;
A. Bassoli
Secondo
;
L. Merlini;
1994

Abstract

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.
Settore CHIM/10 - Chimica degli Alimenti
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/180820
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