Identification of the sex pheromone of the yellow scale

1979 ◽  
Vol 5 (1) ◽  
pp. 27-33 ◽  
Author(s):  
M. J. Gieselmann ◽  
D. S. Moreno ◽  
J. Fargerlund ◽  
H. Tashiro ◽  
W. L. Roelofs
Keyword(s):  
1972 ◽  
Vol 65 (2) ◽  
pp. 443-446 ◽  
Author(s):  
D. S. Moreno ◽  
G. E. Carman ◽  
R. E. Rice ◽  
J. G. Shaw ◽  
N. S. Bain
Keyword(s):  

1982 ◽  
Vol 69 (7) ◽  
pp. 348-348 ◽  
Author(s):  
W. L. Roelofs ◽  
M. J. Gieselmann ◽  
K. Mori ◽  
D. S. Moreno

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.


2019 ◽  
Vol 112 (2) ◽  
pp. 665-670
Author(s):  
Luo Zongxiu ◽  
Cai Xiaoming ◽  
Li Zhaoqun ◽  
Bian Lei ◽  
Xin Zhaojun ◽  
...  
Keyword(s):  

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