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

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