Interesting Transformations of Thiocamphor

Abstract

Thiocamphor has been found to furnish bornane, camphor, isoborneol, isobornylthiol, bornylthiol, tetrahydro-bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-disulfide, and three isomeric bis-(1,7,7-trimethylbicyclo[2.2.1]heptyl)-3,3′-dithiols when treated with NaBH₄ either in dry THF or dry diethylene glycol diethyl ether. The origins of the above interesting compounds and their mass spectral characterization are presented in this article.

Keywords:

• GC-MS
• mass spectrometry
• pathway
• radicals