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J Chem Ecol

Title:		"Replacement of carcinogenic alkylating agent ethylene oxide in the synthesis of (Z)-3-dodecen-1-YL (E)-2-butenoate, sex pheromone of sweet-potato weevil,Cylas formicarius elegantulus (summers) andCylas formicarius formicarius (F.)"
Author(s):		Lo CC; Hung MD; Liu CJ;
Address:		"Pesticide Chemistry Department, Taiwan Agricultural Chemical and Toxic Substances Research Institute (TACTRI), Taiwan R.O.C."
Journal Title:		J Chem Ecol
Year:		1992
Volume:		18
Issue:		2
Page Number:		95 - 103
DOI:		10.1007/BF00993745
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"An alternative synthesis of (Z)-3-dodecen-1-y1 (E)-2-butenoate without use of carcinogenic ethylene oxide and HMPA is described. By coupling of the tetrahydropyranyl (THP) ether of 3-butyn-1-ol with 1-bromooctane with sodamide in liquid ammonia, 12-(2-tetrahydropyranyloxy)-9-dodecyne was obtained; subsequent hydrolysis and semihydrogenation afforded (Z)-3-dodecen-1-ol. The alcohol was then reacted with crotonyl chloride to give the desired crotonate with a total yield of 29.8%. Males of sweet-potato weevil,Cylas formicarius were strongly attracted to the synthetic sex pheromone. The attraction from the dispenser of polyethylene tube was better than the attraction from the dispenser of rubber septum in the field"
Keywords:
Notes:		"PubMed-not-MEDLINELo, C C Hung, M D Liu, C J eng 1992/02/01 J Chem Ecol. 1992 Feb; 18(2):95-103. doi: 10.1007/BF00993745"