Hetero-Diels-Alder reactions of chlorodithioformates with acyclic 1,3-dienes

Abstract

At elevated temperatures chlorodithioformates 1 react with acyclic 1,3-dienes 2 with remarkable regioselectivity to yield 2H-3,6-dihydrothiopyrans 3. Spontaneous loss of HCl from 3 leads to the isolable but labile 2H-thiopyrans 4.

A convenient access to ring unsaturated cyclopentanecarbodithioates via hetero-Diels–Alder chemistry

“…Following earlier work on hetero-Diels-Alder reactions of chlorodithioformates, including 1, with acyclic 1,3-dienes 8 we have now found that the corresponding reactions of 1a 9a and 1b 9b (cf.…”

Sulfur, An Important Element in my Life

“…In one of our most recent papers we could show that, at elevated temperatures, chlorodithioformates 7 do react with simple alka-1,3-dienes to give the corresponding Diels-Alder adducts [126]. For reactions of chlorodithioformates 7 leading to C-sulfonyldithioformates 54, see Section 7.5.…”