Sila-Riechstoffe und Riechstoffe-Isostere. 11. Mitt. Vergleich von Carbinolen und Silanolen mit Thiocarbinolen und Silanthiolen

Abstract

The thiocarbinolsRC(CH3)2SH withR=C6H5CH2 and C6H5CH2CH2 were prepared via reactions 2–5 and compared in their odors (very unpleasant) with the fragrances of the analogous carbinolsRC(CH3)2OH and silanolsRSi(CH3)2OH. Silanethiols, prepared by reactions 6–8, smell less unpleasant than thiocarbinols but decompose easily in the presence of catalytic amounts of ammonium salts (eq. 9). Very pure hexenyl-methyl-vinylsilanethiol (“silathiolinalool”) decomposes contrarily under cyclization to a 1-sila-2-thia-cyclopentane derivative (E 1). The differences of odors, in spite of very similar structures, are discussed in the light of the theory ofAmoore (“Size and structure of molecules rule their odor qualities”).