The chemistry of small ring compounds. Part 41: Methylenethiirane, an isomer of cyclopropanethione

Abstract

Abstract The cyclic carbonate 3, prepared from bis(1‐hydroxycyclopropyl) sulfide and phosgene, has been thermolysed at 500° and 0.5 mm, yielding methylenethiirane (4), an isomer of cyclopropanethione. The structure of 4 is supported by mass spectrometry, 1 H‐ and 13 C‐NMR and infrared (in vapour phase and in solution). Attempted reactions with methyl fluorosulfate, diazomethane, triphenylphosphine and 1,3‐diphenylisobenzofuran all lead to polymeric material of uncertain structure.