Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 66, Issue 16, Pages 5595-5600Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo001571c
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alpha-(Benzotriazolyl)methyl thioethers la-e reacted with styrenes under Lewis acid catalysis to give novel polysubstituted thiochromans (3,4-dihydro-2H-1-benzothiopyrans) 3-14 and 16-20 in generally high yields. Most thiochromans were isolated as one diastereomer following recrystallization. The configuration and conformation of the products are predicted on the basis of their NMR data. A stepwise reaction, proceeding via a [4(+) + 2] cationic polar cycloaddition mechanism, is proposed.
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