Oxido compds 2- ethylenealcohols

Without additional reagents 2- thylenealcohols from oxido compds. s. 28, 4 2 -functionalized 2-ethylenealcohols s. A.A. Gevorkyan et al., Khim. Geterotsikl. 

Ethylenealcohols from oxido compds. Abnormal ring opening... 

A soln. of cyclooctene oxide in benzene passed at 180 with the aid of Ng through a column packed with Li-orthophosphate pellets 3-hydroxycyclooctene. Y 70%. - Li-diethylamide causes mostly rearrangement to 2-hydroxybicyclo[3.3.0]-octane. M. N. Sheng, Synthesis 1972, 194 allyl alcohol from propylene oxide s. A. G. Polkovnikova, N. S. Usacheva, and A. E. Folomeeva, Khim. Prom. 49, 325 (1973) C. A. 79, 31412 2-ethylenealcohols preferably with Li-di-n-propylamide or Li-di-n-butylamide s. C. L. Kissel and B. Rickborn, J. Org. Chem. 37, 2060 (1972) by thermal rearrangement without added acids or bases s. R. J. Anderson et al., Am. Soc. 94, 5379 (1972) basic rearrangements of oxido compds., review s. V. N. Yandovskii and B. A. Ershov, Russ. Chem. Rev. 41, 403 (1972) (Eng. transl.). 

Without additional reagents Simultaneous formation of 1,2-halogenhydrins and 2-ethylenealcohols from oxido compds. 

An 8%-soln. of HCl in glacial acetic acid added to soln. of 16i -methyl-6a,7a 16a, 17a-bisoxido-4-pregnene-3,20-dione in acetic acid, and stirred 6 hrs. at room temp. -> 6i -diloro-7a, 17a-dihydroxy-16-methylene-4-pregnene-3,20-dione. Y 87.1%. F. e., also formation of glycols, s. E. L. Shapiro et al., J. Med. Chem. 15, 716 (1972) 2-ethylenealcohols from oxido compds. by a mild, almost neutral, method with diphenyl diselenide (Caution Se-compds. are toxic) cf. K. B. Sharpless and R. F. Lauer, Am. Soc. 95, 2697 (1973). 

Lithium/liq. ammonia/ammonium chloride 3-Ethylenealcohols from 2,4-dienones with formation of alcohols from oxido compds. Stereospecific reduction... 

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