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

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.
Rossi, Renzo; Carpita, Adriano; Gaudenzi, L; Quirici, M. G.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/245886
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