A thermal dimerisation of the Diels–Alder type is reported for certain 3-aryl-2-cyanothioacrylamides giving rise to novel derivatives of 3,4-dihydro-2H-thiopyran. The regioselectivity and stereoselectivity of this thermal heterodiene cycloaddition reaction are rationalised in terms of frontier orbital interactions. N.m.r. and i.r. data are reported for 21 thioacrylamides in monomeric and/or dimeric form.
No takes yet. Share an insight, caveat, or question.
Brunskill et al. (1978) studied this question.