Abstract
Iodine-catalyzed cyclocondensation of cinnamaldehyde and thiophenol yields rapidly trans-2-phenyl-4-thiophenoxy-3,4-dihydro-2H-1-benzothiopyran in excellent yield with very high diastereoselectivity.
Highlights
Iodine-catalyzed cyclocondensation of cinnamaldehyde and thiophenol yields rapidly trans-2-phenyl-4-thiophenoxy-3,4-dihydro-2H-1-benzothiopyran in excellent yield with very high diastereoselectivity
A survey of the literature shows that there are a variety of methods available for the synthesis of these compounds, among which the reaction of thiophenols with α,β-unsaturated aldehydes [2,3] or allyl alcohols [4] in presence of various acidic catalysts are important
The conjugate addition of thiophenol to α,β-unsaturated ketones has been reported to be catalyzed by iodine [5]
Summary
Abstract: Iodine-catalyzed cyclocondensation of cinnamaldehyde and thiophenol yields rapidly trans-2-phenyl-4-thiophenoxy-3,4-dihydro-2H-1-benzothiopyran in excellent yield with very high diastereoselectivity. A survey of the literature shows that there are a variety of methods available for the synthesis of these compounds, among which the reaction of thiophenols with α,β-unsaturated aldehydes [2,3] or allyl alcohols [4] in presence of various acidic catalysts are important.
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