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8685221 
Journal Article 
Alicyclic glycols. Part XII. Derivatives of cycloHeptane-1: 2-diol 
Owen, LN; Saharia, GS 
1953 
Yes 
Journal of the Chemical Society
ISSN: 0368-1769 
2582-2588 
English 
Some monoesters, simple diesters, and mixed diesters of cis- and of trans-cycloheptane-1 : 2-diol have been prepared. trans-2-Chloro-, -2-bromo-, and -2-iodo-cycloheptanol are obtained by fission of cycloheptene oxide with the corresponding hydrogen halide and also by reaction of the monotoluene-p- sulphonate of the trans-diol with lithium chloride, lithium bromide, and sodium iodide, respectively; a trans-halogenohydrin is also obtained by reaction of the monotoluene-p-sulphonate of the cis-diol with the appropriate metal salt. With calcium carbonate and aqueous acetone, trans-2-acetoxy-cycloheptyl toluene-p-sulphonate gives cis-2-acetoxycycloheptanol; an ethyl ether, also, is formed when ethanol is the solvent. The trans-monotoluene-p-sulphonate reacts with alkali much more rapidly than does the cis-isomer; the products are cycloheptene oxide and cycloheptanone, respectively. Comparison with the corresponding cyclopentane and cyclohexane derivatives shows that for the cis- and for the trans-monotoluene-p-sulphonates of the 1 : 2-diols the order of reactivity towards alkali is cyclopentane > cycloheptane > cyclohexane.