As part of a study’ of derwatwes of dlglycolaldehyde (2,2’-ouyblsacetaldehyde), the renctlon between dwJycolaldehyde bls(dlethy1 dlthloacetal)’ ’ (1) and alcohols has been studled The acychc (2a-d) and cychc (3a-b) products are noted m Table I Primaryalcohols gave only the acychc acetals 2a-c, 2-propanol gave both acychc (2d) and cychc (3a) acetals, and rerf-butyl alcohol gave the cyc11c acetal 3b
α-substitution of the thiol. The acyclic dithioacetal 2a was the only product isolated when methanethiol was used, but mixtures of acyclic dithioacetals, cis -2,6-bis(alkylthio)-1,4-dioxanes, and trans -2,6-bis(alkylthio)-1,4-dioxanes were obtained when ethanethiol, 1-propanethiol, and 2-propanethiol were used. From 1a and 2-methylpropane-2-thiol, the acyclic dithioacetal 2e and the cis (7) and trans (8) stereoisomers