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  • 1
    Electronic Resource
    Electronic Resource
    Replacement of carcinogenic solvent HMPA by DMI in insect sex pheromone synthesis (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 3245-3253 
    Details
    ISSN: 1573-1561
    Keywords: Smaller tea tortrix ; Adoxophyes fasciata ; (Z)-9-tetradecenyl acetate ; (Z)-11-tetradecenyl acetate ; (E)-11-tetradecenyl acetate ; 10-methyl-dodecyl acetate ; hexamethylphosphoric triamide ; 1,3-dimethyl-2-oxo-hex-ahydropyrimidine ; 1,3-dimethyl-2-imidazolidinone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Hexamethylphosphoric triamide (HMPA) is a good solvent for the alkylation of terminal acetylenes; however, it has been proven to be a carcinogen towards rats and should be considered as a serious risk to man when a large-scale synthesis is involved. Thus the search for a safe alternative is important. The physical properties of 1,3-dimethyl-2-imidazolidinone (DMI) are similar to DMPU (1,3-dimethyl-2-oxo-hexahydropyrimidine) and HMPA, but the potential toxicological risk of DMI is less than DMPU and HMPA. When used in the alkylation of terminal acetylenes, DMI is comparable with HMPA, thus it is a good alternative solvent to the carcinogen HMPA in the alkylation because it provides a safer working environment than DMPU and HMPA.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00982095
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  • 2
    Electronic Resource
    Electronic Resource
    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.) (1992)
    Springer
    Journal of chemical ecology 18 (1992), S. 95-103 
    Details
    ISSN: 1573-1561
    Keywords: Sweet-potato weevil ; Coleoptera ; Curculionidae ; Cylas formicarius ; sex pheromone ; (Z)-3-dodecen-1-yl (E)-2-butenoate ; ethylene oxide ; hexamethylphosphoric triamide ; 3-butyn-1-ol ; liquid ammonia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: 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.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00993745
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