MONOFLUORO ANALOGS OF EUGENOL METHYL-ETHER AS NOVEL ATTRACTANTS FOR THE ORIENTAL FRUIT-FLY

被引:41
作者
KHRIMIAN, AP
DEMILO, AB
WATERS, RM
LIQUIDO, NJ
NICHOLSON, JM
机构
[1] USDA ARS,BELTSVILLE AGR RES CTR,BELTSVILLE,MD 20705
[2] USDA ARS,TROP FRUIT & VEGETABLE RES LAB,HILO,HI 96720
关键词
D O I
10.1021/jo00105a019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Monofluoro analogs of eugenol methyl ether as potential attractants for the Oriental fruit fly (Bactrocera dorsalis, Hendel) were synthesized using selective fluorination reactions: electrophilic hydro- and iodofluorination, fluorodehydroxylation with (diethylamido)sulfur trifluoride (DAST), and Wittig fluoroolefination through the stabilized ylides. Unusual reduction of the double bond was detected in a reaction of eugenol methyl ether with pyridinium poly(hydrogen fluoride). Bis-[(3,4-dimethoxyphenyl)alkyl] carbonates were identified as the novel nucleophilic substitution products of the intermediate generated from the reaction of 3,4-dimethoxybenzenealkanols with DAST. Reductive desulfonylation of fluorovinyl sulfone 24-(Z) with sodium amalgam afforded 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene (E/Z = 85:15) which was highly attractive to the Oriental fruit fly.
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页码:8034 / 8039
页数:6
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