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Abstract
Cyclohexane 1,2-diol (1) has been phosphorylated to the cyclic phosphorochloridate (2; X = O) and chloridothioate (2; X = S). Hydrolysis of the former with boiling aqueous acetone gave 2-hydroxycyclohexyl dihydrogen phosphate (3; X = O, R = H) and excess isopropyl alcohol gave the diisopropyl phosphate (3; X = O, R = (CH3)2CH). Reaction of the chloridate (2; X = O) with aniline, diethylamine, and morpholine gave the corresponding amidates (4–6). The chloridothioate (2; X = S) similarly gave amidates (8, 9) with morpholine and aniline, but with isopropyl alcohol the cyclic isopropyl phosphate (10) was obtained. Attempted hydrolysis (aqueous acetone) of the chloridothioate (2; X = S) resulted in decomposition. Salicylic acid (11) with phosphorus oxychloride gave the cyclic phosphorochloridate (12) which reacted with ethanol, propanol, isopropyl alcohol and benzyl alcohol to give the alkoxy derivatives (13–16). The highly sterically hindered alcohols, t-butanol and benzhydrol did not react. The alkoxy derivatives were hydrolyzed to the corresponding 2-carboxyphenyl phosphates (17–20). Attempted reaction of the chloridate (12) with aniline gave complex mixtures of unidentified products. The proton n.m.r., i.r. and ms. of the compounds (12–20) are briefly discussed.