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1％二乙烯基苯交联的聚苯乙烯树脂在N,N,N′,N′-四甲基乙二胺的存在下用丁基锂进行锂化后与二苯基二氯硅烷反应制得聚苯乙烯支持的三苯基氯硅烷(2).这种聚合物用于一些鳞翅目(Lepidoptera)昆虫的性信息素的固相合成.2与1,9-壬二醇、1,10-癸二醇和1,12-十二碳二醇反应分别生成聚合物支持的二醇单硅醚(4a、4b、4c),游离的醇基用Swern试剂(DMSO和草酸酰氯)氧化成聚合物支持的醛(5a、5b、5c),经Wittig缩合反应和用氟离子裂解后分别得到9-十四碳烯醇-1(8a),10-十四碳烯醇-1(8b)和12-十四碳烯醇-1(Sc).化合物8经乙酰化后分别得到9-十四碳烯醇-1乙酸酯(9a),其顺式异构体是秋灰夜蛾(S.frugiperda,Smith)的性信息素;10-十四碳烯醇-1乙酸酯(9b),其顺式异构体是橡卷叶蛾(A.semiferamus,Walker)的性信息素;和12-十四碳烯醇-1乙酸酯(9c).9c与四氯化碲反应,硫化钠还原后转化成E-和Z-异构体比例为54∶46的亚洲玉米螟(Ostrinia furnicalis)的性信息素.
1% divinylbenzene cross-linked polystyrene resin was lithiated with butyllithium in the presence of N, N, N ’, N’-tetramethylethylenediamine and reacted with diphenyldichlorosilane Polystyrene-supported triphenylchlorosilane (2) This polymer is used in the solid-phase synthesis of sex pheromone of some Lepidoptera insects.2 Compatible with 1,9-nonanediol, 1, The reaction of 10-decanediol with 1,12-dodecanediol produces the polymer-supported diolmonosilicone (4a, 4b, 4c), respectively. The free alcohol groups are oxidized with Swern reagent (DMSO and oxalic acid chloride) The aldehyde (5a, 5b, 5c) supported by the reaction of 9-tetradecenol-1 (8a), 10-tetradecen- 1-enol- 12-tetradecenol-1 (Sc) .After acetylation of compound 8, 9-tetradecenoyl alcohol-1 acetate (9a) frugiperda, Smith); 10-tetradecenol-1 acetate (9b) whose cis isomer is a sex pheromone of A. semiferamus (Walker); and 12- Tetradecenol-1 acetate (9c) .9c reacts with tellurium tetrachloride, sodium sulfide is reduced and converted to the E- and Z-isomer ratio of 54:46 Of the sex pheromone of Ostrinia furnaricis.