Abstract
Treatment of dimethyl 3-phenyl-2-propynylsulfonium bromide (I) with cyclohexanone in the presence of sodium hydride gave methyl 2-phenyl-4-(1-hydroxycyclohexyl)-2, 3-butadienyl sulfide (II), which accompanied with the rearrangement of SNi' type. Similarly, I reacted with cyclopentanone to give a mixture of methyl 2-phenyl-4-(1-hydroxycyclopentyl)-2, 3-butadienyl sulfide (III) and methyl 2-phenyl-4-(1-hydroxycyclopentyl)-3-butynyl sulfide (IV). Dimethyl 2-butynylsulfonium bromide (V), likewise, reacted with cyclohexanone and cyclopentanone to afford methyl 2-methyl-4-(1-hydroxycyclohexyl)-2, 3-butadienyl sulfide (VI) and methyl 2-methyl-4-(1-hydroxycyclopentyl)-2, 3-butadienyl sulfide (VII), respectively. On the other hand, treatment of dimethyl 2-propynylsulfonium bromide (VIII) with cyclohexanone and cyclopentanone gave methyl 4-(1-hydroxycyclohexyl)-3-butynyl sulfide (X) and methyl 4-(1-hydroxycyclopentyl)-3-butynyl sulfide (XIII), respectively.
