The cis epoxy ether 11 reacted very rapidly (1 min) to give the product distribution shown in eq 4 in overall 95% yield. The acetate of 12 had nmr 0.85 (d, J = 7 Hz, 3), 0.9-2.1 (m, 7), 2.02 (s, 3), 3.31 (s, 3), 3.48 (m, 1), and 4.38 ppm (d of d, J = 1.4, 10.1 Hz, 1). The acetate of 13 had nmr 0.97 (d, J = 7 Hz, 3), 0.9-2.3 (m, 7), 1.98 (s, 3), 2.75 (t of d, J = 4.7, 11 Hz, 1), 3.31 (s, 3), and 4.38ppm (t of d, J = 4.7, 11 Hz, 1).The trans epoxy ether 14 after 3 hr at -5°and 2.5 hr at 25°g ave 83% of a mixture having the composition shown in eq 5. The acetate of 15 had nmr 5 0.90 (d, J = 7 Hz, 3), 0.9-2.2 (m, 7), 2.00 (s, 3), 3.01 (m, 1), 3.22 (s, 3), and 4.48 (t, J = 10 Hz, 1). The acetate of 16 had 0.94 (d, J = 7 Hz, 3), 0.9-2.1 (m, 7), 1.96 (s, 3), 3.29 (s, 3), 3.33 (m, 1), and 4.74 ppm (t of d, J = 4.3 and 10.0 Hz, 1).cis-2,3-Epoxy cyclohexyl acetate (17) after 40 min at -7°g ave 89% of a mixture containing 6% unreacted 17, 29% of 612 (identical with material formed in eq 2), 7% of a compound

The synthesis of yomogi alcohol (2,5,5-trimethyIhepta-3,6-dien-2-01, 2) is described, and experiments directed towards its allylic rearrangement to artemisia alcohol derivatives have been carried out. Acidic reagents open thc ring of yomogi alcohol epoxide (16) and with participation of the 6,7-double-bond, a shift of the vinyl group results to yield a compound with the santolinyl skeleton. The same rcagents are without effect when this double bond is reduced. Action of butyllithium on the benzaldehyde acetal (41) of 2,5-dimethyl-4-vinyl-2, 3dihydroxy-hex-5-ene (28), obtained by acid-catalyzed ring opening of yomogi alcohol epoxide in the presence of benzaldehyde, leads to santolinatriene (42).This vinyl shift is not observed in the case of 0-acetyy yomogi alcohol epoxide (46), from which a compound believed to be an oxetan 48 (R = COCH,) is formed with coneomitent shift of the acetate group. Further unusual reactions of the oxetan are described, and some observations about the epoxiclation of sterically hindered ally1 alcohols and their acetates are made. l) 2,Ce travail a fait I'objet d'une Communication priliminaire [l]. Pour la premiiire publication de cette sirie voir [2].

Z‐Formyl‐cyclododecanon (Ia) liefert das Chlorderivat (Ib), das mit Natriumcarbonat . zu (II) kondensiert wird.

Das bei der Umsetzung von 3‐Methyl‐buten‐(2)‐ylchlorid mit Magnesium erhältliche Dien (I) wird durch sensibilisierte O2‐Oxidation in Gegenwart von Licht und anschließende Reduktion der Hydroperoxide mit Na‐sulfit in ein 4:1‐Gemisch aus Yomogialkohol (II) und dem Dienol (III) übergeführt.