Advances in Acarology. Vol. II, edited by John A. Naegele. Cornell University Press, Ithaca, 1965 (Dec. 17). x + 174 pp.; 25 plates. Price 9.75 U.S. dollars. - Insect Sex Attractants, by Martin Jacobson. John Wiley and Sons, Inc., New York, 1965. xi + 154 pp. Price 7.75 U.S. dollars.

1966 ◽  
Vol 98 (10) ◽  
pp. 1119-1120
Author(s):  
Evert E. Lindquist ◽  
J. A. Downes
Keyword(s):  
New York ◽  
Sex Attractants ◽  
Cornell University ◽  
Insect Sex Attractants ◽  
Insect Sex

Insect Sex Attractants. VII. 5,9-Tridecadien-1-ol Acetates

1967 ◽  
Vol 10 (6) ◽  
pp. 1190-1191 ◽  
Author(s):  
David. Warthen ◽  
Martin. Jacobson
Keyword(s):  
Sex Attractants ◽  
Insect Sex Attractants ◽  
Insect Sex

The use of polymer supports in organic synthesis. XII. The total stereoselective synthesis of cis insect sex attractants on solid phases

1977 ◽  
Vol 55 (23) ◽  
pp. 4135-4143 ◽  
Author(s):  
Thomas M. Fyles ◽  
Clifford C. Leznoff ◽  
John Weatherston
Keyword(s):  
Stereoselective Synthesis ◽  
Coupling Reaction ◽  
Ethyl Bromide ◽  
Butyl Bromide ◽  
Sex Attractants ◽  
Polymer Supports ◽  
Acid Cleavage ◽  
Insect Sex Attractants ◽  
Internal Alkynes ◽  
Insect Sex

A 2% crosslinked divinylbenzene-styrene copolymer, incorporating trityl chloride groups (2) was used in the synthesis of insect sex attractants of Lepidoptera by a two-step alkyne coupling route. Polymer 2 reacted with the symmetrical diols, 1,8-octanediol and1,10-decanediol, to give the monoblocked polymer-bound diols 5 and 6 respectively. Mesylation of 5 and 6 gave the polymer-bound monomesylates 7 and 8 which on coupling with lithioacetylide gave the polymer-bound terminal alkynes 9 and 10 respectively. Acid cleavage of 9 and 10 provide 9-decyn-1-ol and 11-dodecyn-1-ol respectively. A second coupling step was performed by lithiation of 9 and 10 with n-butyllithium or tert-butyllithium followed by treatment with n-butyl bromide or ethyl bromide to give polymer-bound internal alkynes, which on acid hydrolysis gave 9-tetradecyn-1-ol (22), 11-hexadecyn-1-ol (23), and 11-tetradecyn-1-ol (24). If 10 had been lithiated with n-butyllithium and coupled with ethyl bromide, some translithiation occurred to liberate n-butyl bromide which entered into the coupling reaction eventually giving a mixture of 23 and 24. This problem was resolved by the use of tert-butyllithium in the lithiation step. Attempts were made to reduce polymer-bound internal alkynes stereoselectively to cis-alkenes with 9-borabicyclononane, diisobutylaluminum hydride, and catechol borane but all these reagents proved inadequate due to incomplete reduction, overreduction, hydrogenolysis of the alkyne from the polymer, and non-selectivity. Polymer-bound internal alkynes were quantitatively reduced exclusively to cis insect sex attractants using disiamylborane without concurrent overreduction or hydrogenolysis.

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