ChemInform Abstract: Rapid Assembly of Polycyclic Structures via Sigmatropic Rearrangement of S‐Propargyl Xanthates.

Abstract

Propargyl xanthates undergo rearrangement to afford intermediary bis(alkylidene)dithiolanones which are trapped by Diels-Alder cycloaddition to yield dithiolones, representing three new carbocycle types such as (II), (VIII), and (X). The approach is not limited to scaffolds containing a rigid aryl backbone, but may also be applied to systems incorporating aliphatic and heteroaliphatic skeletons like propargyl xanthates (XI). Under similar conditions tetrahydrofuran, -pyran, pyrrolidine, and piperidine heterocyclic structures can be obtained. -(HARRINGTON, R. M.; WRIGHT, D.; ZARD*, S. Z.; Heterocycles 86 (2012) 2, 965-971, http://dx.doi.org/10.3987/com-12-s(n)98 ; Dep. Chem., CNRS, Ec. Polytech., F-91128 Palaiseau, Fr.; Eng.) -H. Hoennerscheid