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    Intermediates in the preparation of 2,2-dimethyl-3-aryl-cyclopropanecarboxylic acids and esters
    1.
    发明授权
    Intermediates in the preparation of 2,2-dimethyl-3-aryl-cyclopropanecarboxylic acids and esters 失效
    中间体制备2,2-二甲基-3-芳基 - 环丙烷羧酸和酯

    公开(公告)号：US4681952A

    公开(公告)日：1987-07-21

    申请号：US669182

    申请日：1984-11-07

    申请人： Reinhard Lantzsch ,  Dieter Arlt ,  Manfred Jautelat

    发明人： Reinhard Lantzsch ,  Dieter Arlt ,  Manfred Jautelat

    IPC分类号： C07C69/753 ,  C07C45/00 ,  C07C45/63 ,  C07C45/65 ,  C07C45/68 ,  C07C49/223 ,  C07C49/587 ,  C07C49/657 ,  C07C49/683 ,  C07C49/697 ,  C07C49/753 ,  C07C51/00 ,  C07C61/39 ,  C07C61/40 ,  C07C67/00 ,  C07C201/00 ,  C07C205/55 ,  C07C227/00 ,  C07C227/02 ,  C07C229/46 ,  C07C253/00 ,  C07C255/56 ,  C07C255/57 ,  C07C313/00 ,  C07C315/04 ,  C07C317/24 ,  C07C317/44 ,  C07C319/20 ,  C07C323/62 ,  C07D307/46 ,  C07D307/54 ,  C07D307/56 ,  C07D307/68 ,  C07D307/70 ,  C07D333/24 ,  C07D333/28 ,  C07D333/38 ,  C07D333/42 ,  C07F7/08 ,  C07D307/02 ,  C07D333/16

    CPC分类号： C07D307/56 ,  C07C45/63 ,  C07C45/65 ,  C07C45/68 ,  C07C49/223 ,  C07C49/657 ,  C07C49/683 ,  C07C49/697 ,  C07C49/753 ,  C07C51/00 ,  C07D307/68 ,  C07D307/70 ,  C07D333/28 ,  C07D333/38 ,  C07D333/42

    摘要： A process for the preparation of 2,2-dimethyl-3-arylcyclopropanecarboxylic acid or ester of the formula ##STR1## in which Ar is naphthyl or the radical ##STR2## R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, Z is oxygen, sulphur, or 1,2-ethenediyl, andR.sup.2 represents hydrogen, halogen, cyano, nitro or trialkylsilyl or a radical, which is optionally substituted by halogen, from the series comprising alkyl, cycloalkyl, alkenyl, alkoxy, alkylenedioxy, alkylthio, alkylsulphinyl, alkylsulphonyl, dialkylamino, phenyl and phenoxy,comprising reacting a 1-aryl-1-halogeno-2,2-dimethyl-3-butanone of the formula ##STR3## in which X.sup.1 is chlorine or bromine, with a base in the presence of a diluent at a temperature between about -20.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-arylcyclobutanone of the formula ##STR4## and reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +50.degree. C., reacting such 2,2-dimethyl-3-arylcyclobutanone with chlorine or bromine in the presence of an inert diluent at a temperature between about -30.degree. and +150.degree. C., thereby to form a 2,2-dimethyl-3-aryl-4-halogenocyclobutanone of the formula ##STR5## and reacting such 2,2-dimethyl-3-aryl-4-halogenocyclobutanone with an alkali metal alcoholate in the presence of an organic solvent or with an alkali metal or alkaline earth metal hydroxide or carbonate in the presence of water and an organic solvent, at a temperature between about -20.degree. and +100.degree. C. The various intermediates are new and the end product is a known intermediate for known insecticides.

    摘要翻译： 制备2,2-二甲基-3-芳基环丙烷羧酸或其中Ar为萘基或R 1为R 1的式“IMAGE”的酯的方法为H或C 1 -C 4 - 烷基，Z为氧，硫 或1,2-乙烯二基，R 2代表氢，卤素，氰基，硝基或三烷基甲硅烷基或任选被卤素取代的基团，包括烷基，环烷基，烯基，烷氧基，亚烷基二氧基，烷硫基，烷基亚磺酰基，烷基磺酰基 ，二烷基氨基，苯基和苯氧基，包括使X1为氯或溴的式“IMAGE”的1-芳基-1-卤代-2,2-二甲基-3-丁酮与碱在稀释剂存在下反应 在约-20℃至+ 150℃之间的温度下，由此形成下式的2,2-二甲基-3-芳基环丁酮，并使这种2,2-二甲基-3-芳基环丁酮与氯或溴反应 在惰性稀释剂存在下，在-30℃〜+ 50℃的温度下，使这样的2,2-二甲基-3-芳基 氯丁酮与氯或溴在惰性稀释剂存在下，在约-30℃至+ 150℃之间的温度下反应，由此形成下式的“2,2-二甲基-3-芳基-4-卤代环丁酮” 并在有机溶剂或碱金属或碱土金属氢氧化物或碳酸盐存在下，在水和有机溶剂的存在下，使这种2,2-二甲基-3-芳基-4-卤代环丁酮与碱金属醇盐反应， 在约-20℃至+ 100℃之间的温度下。各种中间体是新的，最终产物是已知杀虫剂的已知中间体。

    Preparation of 3-vinyl-substituted 2,2-dimethylcyclopropane-1-carboxylic acids and esters and intermediates therefor
    3.
    发明授权
    Preparation of 3-vinyl-substituted 2,2-dimethylcyclopropane-1-carboxylic acids and esters and intermediates therefor 失效
    制备3-乙烯基取代的2,2-二甲基环丙烷-1-羧酸及其酯及其中间体

    公开(公告)号：US4992577A

    公开(公告)日：1991-02-12

    申请号：US355578

    申请日：1989-05-22

    申请人： Reinhard Lantzsch ,  Dieter Arlt ,  Manfred Jautelat

    发明人： Reinhard Lantzsch ,  Dieter Arlt ,  Manfred Jautelat

    IPC分类号： C07C45/63 ,  C07C45/72 ,  C07C49/227 ,  C07C49/235 ,  C07C51/00

    CPC分类号： C07C45/72 ,  C07C45/63 ,  C07C49/227 ,  C07C49/235 ,  C07C51/00

    摘要： A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.

    摘要翻译： 制备式（I）化合物的方法，其中Y为卤素，任选被卤素或C 1-4 - 烷氧基取代的烷基或环烷基，任选被卤素，芳基，杂芳基或烷氧基羰基取代的链烯基，X为氢 ，卤素或任选的卤素取代的烷基，或X和Y与相邻的C原子一起形成具有至多6个C原子的饱和环烷基环，R是氢或C 1 -C 4烷基，包括使 式（II）化合物与式（III）的2-甲基丁-3-酮在氢卤酸存在下反应，从而形成4,4-二甲基-3-卤代-1-己烯-5 其中Hal是卤素的式（Ⅳ）化合物，卤化所述化合物以制备下式化合物（Ⅴ），并使所述化合物与式R-OM（Ⅵ）的碱反应在 其中M为1当量碱金属或碱土金属离子。 化合物IV和V是新的。 通过合适的条件选择性地制备反式异构体。