Studies on Organic Fluorine Compounds. XIX. Synthesis and Reactions of"Dewar"Thiophene

Abstract

The structure of photo isomer of 2, 3, 4, 5-tetrakis (trifluoromethyl) thiophene (I) was determined as "Dewar" type (II) by ¹³C-NMR (nuclear magnetic resonance) and other physical and chemical data. Diels-Alder reaction of II with furans gave exo-exo type products, 10-oxa-4-thiatetracyclo[5.2.1.0^{2, 6}.0^{3, 5}]dec-8-ene derivatives (VI), which was derived to substituted oxahomocubanes, 9-oxapentacyclo[4.2.1.0^{2, 5}.0^{3, 8}.0^{4, 7}]nonanes (VIII) by successive desulfurization and photochemical reactions.