Prins Reactions of Arylaldehydes, V: On the Reaction with 2-Butene and with Cyclohexene

Article abstract of DOI:10.1007/BF00905070

By reaction of 2-<(1RS,2RS)-2-hydroxy-1-methyl-propyl>-2-phenyl-1,3-dithiane (1a) with cis-2-butene oxide, subsequent reduction and acetalization c-4,t-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3a) and t-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3b) were synthesized as model compounds.For the same purpose by aldol reaction of cyclohexanone and reduction (1RS,2SR)-2<(RS)-hydroxy-(4-methoxyphenyl)methyl>cyclohexanol (7a), (1RS,2RS)-2<(SR)-hydroxy-(4-methoxyphenyl)methyl>cyclohexanol (8a), and (1RS,2RS)-2<(RS)-hydroxy-(4-nitrophenyl)methyl>cyclohexanol (8b), and by acetalization (2α,4α,4aβ,8aβ)-2,4-bis(4-methoxyphenyl)hexahydro-4H-1,3-benzodioxin (9a) and (2α,4α,4aα,8aβ)-2,4-bis(4-nitrophenyl)hexahydro-4H-1,3-benzodioxin (10b) were obtained.From Prins reactions, starting with 2-butene 3a, c-4,c-5-dimethyl-r-2,c-6-diphenyl-1,3-dioxane (3c), r-4,t-5-dimethyl-c-6-phenyl-1,3,2-dioxathiane-2,2-dioxide (4), and (2Z,4E)-1,5-diphenyl-4-methyl-2,4-pentadien-1-on (5), and starting with cyclohexene (E)-3-(4-methoxybenzylidene)cyclohexenyl-4-methoxyphenyl ketone (11) have been isolated in low yields. - Keywords: Addition reactions; 1,3-Diols; 1,3-Dioxanes