SYNTHESIS AND PROPERTIES OF SOME O--GLYCOLALDEHYDES

Article abstract of DOI:10.1016/0008-6215(83)88195-6

O-<2,2-Bis(alkylthio)ethyl>glycolaldehydes (1a-e; alkyl = Et, Pr, Prⁱ, Bu^t, and -CH2-, respectively) have been prepared from the corresponding O-<2,2-bis(alkylthio)ethyl>glycolaldehyde dimethyl acetals (2a-e) by acid hydrolysis.In anhydrous 1,4-dioxane in the presence of BF3*(Et2O)2, 1a-c were partially transformed into glycolaldehyde bis(dialkyl dithioacetals), 1d afforded trans-2,6-bis(tert-butylthio)-1,4-dioxane and 3,5-bis(tert-butylthio)-1,4-oxathiane, and 1e did not react.The acetals 2a-e were prepared from the appropriate glycolaldehyde dialkyl dithioacetal by O-alkylation with bromoacetaldehyde dimethyl acetal.