Rapid assembly of polycyclic structures via sigmatropic rearrangement of s-propargyl xanthates

Ryan M. Harrington (1) , David Wright (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

Upon heating in chlorobenzene, propargyl xanthates yield the corresponding 4,5-bis(alkylidene)-1,3-dithiolan-2-ones which are trapped by unactivated olefins in an intramolecular Diels-Alder cycloaddition yielding interesting polycyclic structures.

Domains: Chemical Sciences; Organic chemistry

Ryan M. Harrington, David Wright, Samir Z. Zard. Rapid assembly of polycyclic structures via sigmatropic rearrangement of s-propargyl xanthates. Heterocycles, 2012, 86 (2), pp.965-971. ⟨10.3987/com-12-s(n)98⟩. ⟨hal-00949988⟩