ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Thiophenium-ylides: Synthesis and reactivity

Aleš Machara and Jiří Svoboda

Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic

E-mail: Jiri.Svoboda@vscht.cz

Abstract: The reaction of propanedioic acid, 2-diazo-1,3-bis(1,1-dimethylethyl) ester (di-tert-butyl diazomalonate) with a series of cyclopenta[b]thiophenes in the presence of catalytic rhodium acetate was studied. The resulting S—C ylides underwent a rearrangement to form a heterocycle with different topology; thialene, in very low yields. Experimental and spectral data for all compounds are provided.

Keywords: cyclopenta[b]thiophene – thiophenium-ylide – rhodium catalysis – thialene

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-012-0222-7

Chemical Papers 67 (1) 59–65 (2013)