The Journal of Organic Chemistry

A Facile Skeletal Rearrangement. Reidentification of “2, 2, 4-Trimethylpentane-1, 4-diol” 1

CF Wilcox Jr, DL Nealy

Index: Wilcox,C.F.; Nealy,D.L. Journal of Organic Chemistry, 1963 , vol. 28, p. 3454 - 3457

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Citation Number: 2

Abstract

The compounds previously reported to be 2, 2, 4-trimethylpentane-1, 4-diol and the corresponding dibromide are reidentified as 2, 5-dimethylhexane-2, 5-diol and dibromide, respectively. Synthesis of the authentic 1, 4-diol is reported. From the solvolysis of the related 2, 2, 4-trimethyl-3-penten-l-ol p-toluenesulfonate it is concluded that the erroneous structure assignment resulted from an extremely facile skeletal rearrangement proceeding ...