Angewandte Chemie

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Der Acetylenalkohol 256 entsteht in 47-proz. thyljodid (2M) in fliissigem Ammoniak reagieren l~il]t und das intermedi/~r gebildete 1-Butin (253) nach Zugabe yon Natriumamid mit )iAhylenoxyd (255) umsetzt ~a~}. CH3--CH~--J + Na--C-~CH 251 * CH3--CHs--C~CH 252 253 CH~--CH2 \/ CHa--CH~--C~-CNa + 254 O ~ CH~--CH~--C--~C--CHa--CH2OH 255 256 H \ / H CHa--CH~--C~C--CH~--CH~0H 181 trans-3-Hexenol (261) Den Alkohol (267) gewinnt man am giinstigsten durch LiA1H4-Reduktion der trans-3-Hexens~ture (260a) 9o) oder des entsprechenden ~-thylesters ( 2 6 0 b ) ~ .

C h e m . Soe. 193I, 740. 58) Brand, J. : Bet. D e u t . C h e m . Ges. 27, 806 (1894). , R. F. Mi~ggIer-Chavan, J. P. Marion, D. Reymond u. R. H. Egli: Helv. China. A c t a 50, 1517 (1967); s. d o r t die L i t e r a t u r d e r b i s h e r i g e n U n t e r s u c h u n g e n a u f d i e s e m Gebiet. , n. B. Franck: Angew. C h e m . 67, 303 (1955). 61) Broderich, J. , a n d L. L. ): A m . P. 2 9 5 5 0 4 1 (1960); C. A. 55, 1966 (1961). 6s) Brown, M . : J. Org. C h e m . 33, 162 (1968). 69) Buchi, G.

133) _ _ Die ~ttherischen 01e. IV. A u f l a g e y o n W. Treibs u. K . Bornot, B d . V, S. 374. B e r l i n : A k a d e m i e Verlag 1959. lz4) _ _ Die ~ t h e r i s c h e n 01e. IV. A u f l a g e y o n W. Treibs u. K. Bornot, Bd. V, S. 516, 552, 553 u. 606, B e r l i n : A k a d e m i e Verlag 1959. 135) _ _ Die ~ t h e r i s c h e n 01e. IV. A u f l a g e y o n W. Treibs u. I4. Bornot, B d . V I I , S. 471. B e r l i n : A k a d e m i e Verlag 1961. 136) G i v a u d a n , L. et Cie. S. A . : Niederl.

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