RC≡C(CH2)nOH (I, R = Pr, n = 4, 9; R = Bu, n = 6, 8; R = hexyl, Me; n = 6; R = Et, n = 10) were prepd. by treating RC≡CH with tetrahydropyranyloxyalkyl halides. The redn. of I with Lindlar catalyst gave (Z)-RCH:CH(CH2)nOH, whereas LiAlH4 redn. gave (E)-RCH:CH(CH2)nOH all of which were converted to the acetates. (Z)-6-Nonen-1-ol was obtained by Grignard reaction of (Z)-1-bromo-3-hexene with oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate was obtained by treating 10-tetrahydropyranyloxy-1-decyne with (E)-ClCH2CH:CHMe and Ac2O, followed by hydrogenation of (E)-MeCH:CHCH2C≡C(CH2)8OAc.
Insect sex pheromones. Stereoselective synthesis of several (Z)- and (E)-alken-1-ols, their acetates, and of (9Z,12E)-9,12-tetradecadien-1-yl acetate
ROSSI, RENZO;CARPITA, ADRIANO;
1980-01-01
Abstract
RC≡C(CH2)nOH (I, R = Pr, n = 4, 9; R = Bu, n = 6, 8; R = hexyl, Me; n = 6; R = Et, n = 10) were prepd. by treating RC≡CH with tetrahydropyranyloxyalkyl halides. The redn. of I with Lindlar catalyst gave (Z)-RCH:CH(CH2)nOH, whereas LiAlH4 redn. gave (E)-RCH:CH(CH2)nOH all of which were converted to the acetates. (Z)-6-Nonen-1-ol was obtained by Grignard reaction of (Z)-1-bromo-3-hexene with oxetane. (9Z,12E)-9,12-Tetradecadien-1-yl acetate was obtained by treating 10-tetrahydropyranyloxy-1-decyne with (E)-ClCH2CH:CHMe and Ac2O, followed by hydrogenation of (E)-MeCH:CHCH2C≡C(CH2)8OAc.File in questo prodotto:
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