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    • 3. 发明授权
    • Preparation of 3-vinyl-substituted 2,2-dimethylcyclopropane-1-carboxylic
acids and esters and intermediates therefor
    • 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
    • US4992577A
    • 1991-02-12
    • US355578
    • 1989-05-22
    • Reinhard LantzschDieter ArltManfred Jautelat
    • Reinhard LantzschDieter ArltManfred Jautelat
    • C07C45/63C07C45/72C07C49/227C07C49/235C07C51/00
    • C07C45/72C07C45/63C07C49/227C07C49/235C07C51/00
    • 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.
    • 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。
    • 6. 发明授权
    • 2-(2,2-Dimethyl-3-buten-1-yl)-2-oxazolines
    • 2-(2,2-二甲基-3-丁烯-1-基)-2-恶唑啉
    • US4358598A
    • 1982-11-09
    • US212051
    • 1980-12-01
    • Manfred JautelatDieter Arlt
    • Manfred JautelatDieter Arlt
    • C07D263/04C07D263/12C07D263/10
    • C07D263/04C07D263/12
    • A process comprising reacting a 2-methyloxazoline of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently is hydrogen, alkyl, aralkyl, optionally substituted aryl or two of them together form a ring,with a 3-methyl-2-buten-1-yl derivative of the formula ##STR2## in which X is halide, sulphonate or phosphate, thereby to produce a 2-methyl-3-(3-methyl-2-butenyl)-2-oxazolinium salt of the formula ##STR3## reacting the oxazolinium salt with an alcoholate of the formulaR.sup.5 --O--M (V)in whichM is one equivalent of an alkali metal or alkaline earth metal cation,to produce an oxazolidine of the formula ##STR4## pyrolyzing the oxazolidine to produce a 2-methylene-3-(3-methyl-2-butenyl)-oxazolidine of the formula ##STR5## and heating the 2-methylene-3-(3-methyl-2-butenyl)-oxazolidine to produce a 2-(2,2-dimethyl-3-buten-1-yl)-2-oxazoline of the formula ##STR6## The compounds (II), (III) and (IV) are new.
    • 一种方法包括使式(VI)的2-甲基恶唑啉(其中R 1,R 2,R 3和R 4各自独立地为氢,烷基,芳烷基,任选取代的芳基或其中的两个一起形成环)与3 (VII)的2-甲基-2-丁烯-1-基衍生物,其中X是卤化物,磺酸盐或磷酸盐,从而产生2-甲基-3-(3-甲基-2-丁烯基) - 式(Ⅳ)的2-恶唑啉盐使恶唑啉盐与式为R5-OM(Ⅴ)的醇化物反应,其中M为1当量碱金属或碱土金属阳离子,得到 (III)将式(III)热解得到式(II)的2-亚甲基-3-(3-甲基-2-丁烯基) - 恶唑烷并加热2-亚甲基-3-( 3-甲基-2-丁烯基) - 恶唑烷以制备下式的2-(2,2-二甲基-3-丁烯-1-基)-2-恶唑啉(I)化合物(II),( III)和(IV)是新的。
    • 8. 发明授权
    • Process for the preparation of
2,2-dimethyl-3-vinyl-cyclopropanecarboxylic acids and esters
    • 2,2-二甲基-3-乙烯基 - 环丙烷羧酸和酯的制备方法
    • US4440955A
    • 1984-04-03
    • US443840
    • 1982-11-22
    • Manfred JautelatDieter Arlt
    • Manfred JautelatDieter Arlt
    • C07C49/16B01J23/72B01J23/74B01J27/02B01J27/08B01J27/24B01J31/02B01J31/04B01J31/22C07C43/225C07C45/51C07C45/69C07C51/00C07C61/40C07C69/747
    • C07C45/69C07C43/225C07C45/513C07C51/00
    • A process for the production of 2,2-dimethyl-3-vinyl-cyclopropanecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 is a hydrogen atom, an alkyl group or a radical of an alcohol which can be used in pyrethroids, andX.sup.1 and X.sup.2 each independently is a halogen atom or a fluorine-substituted alkyl radical,comprising adding (a) a polyhalogenoalkene of the formula ##STR2## in which X.sup.3 and X.sup.4 each independently is a halogen atom,to 1-chloro-3,3-dimethyl-pent-4-en-2-one of the formula ##STR3## in the presence of a catalyst which yields free radicals, or in the presence of a metal salt of the VIII main group or of the sub-group IVa, VIIa or Ib of the periodic system, thereby to obtain a mixture of compounds of the formula ##STR4## (b) reacting either or both of such compounds with a base of the formula(R.sup.1 --O.sup..crclbar.).sub.n M.sup.n+in whichM is an alkali metal or alkaline earth metal, andn is 1 or 2.The end products are known insecticides and intermediates therefor, while the intermediates produced by (a) are novel compounds.
    • 制备式“IMAGE”的2,2-二甲基-3-乙烯基 - 环丙烷羧酸衍生物的方法,其中R 1是可用于拟除虫菊酯的氢原子,烷基或醇基,以及 X 1和X 2各自独立地为卤素原子或氟取代的烷基,其包括将(X3)和X4各自独立地为卤素原子的式(a)的多卤代烯烃加入到1-氯-3,3 在产生自由基的催化剂的存在下,或在VIII主族或亚组IVa的金属盐存在下,式“IMAGE”的2-二甲基 - 戊-4-烯-2-酮, VIIa或Ib化合物,从而得到下式化合物的混合物:(b)使这些化合物中的一种或两者与式(R1-O( - ))nMn +的碱反应, 其中M为碱金属或碱土金属,n为1或2.最终产物为已知的杀虫剂及其中间体,而中间体 (a)产生的是新化合物。
    • 9. 发明授权
    • Preparation of 1-aryloxy-methyl ketones
    • 1-芳氧基 - 甲基酮的制备
    • US4399309A
    • 1983-08-16
    • US335942
    • 1981-12-30
    • Manfred JautelatJorg StetterDieter Arlt
    • Manfred JautelatJorg StetterDieter Arlt
    • C07C49/175C07C43/225C07C45/00C07C45/42C07C49/255C07C49/35C07C67/00C07C201/00C07C205/37C07C205/39C07C45/51
    • C07C41/16C07C45/42
    • A process for the preparation of a 1-aryloxy-methyl ketone of the formula ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 each independently is hydrogen, optionally substituted alkyl, alkenyl, alkynyl or optionally substituted aryl, orR.sup.1 and R.sup.2 together are an alkylene chain,R.sup.4 each independently is halogen, alkyl, alkoxy, optionally substituted aryl or nitro, andn is 0, 1, 2 or 3,comprising hydrolyzing a 1-halogeno-2-aryloxy-1-alkene of the formula ##STR2## in which Hal is chlorine or bromine, under acidic conditions at a temperature from about 20.degree. to 150.degree. C. until it is about 95 to 100% complete, adding a base, and then bringing the reaction to completion under weakly alkaline conditions at about 20.degree. to 150.degree. C. Advantageously all stages of the reaction are effected in a single vessel at a temperature from about 40.degree. to 100.degree. C. and in the presence of an inert organic solvent, optionally in admixture with water as a solution or as a two-phase system, about 1 mol of a monobasic acid and 2 mols of alkali metal carbonate being employed per mol of the 1-halogeno-2-aryloxy-1-alkene. The end products are known intermediates for fungicides.
    • 制备式“IMAGE”的1-芳氧基甲基酮的方法,其中R 1,R 2和R 3各自独立地为氢,任选取代的烷基,烯基,炔基或任选取代的芳基,或者R 1和R 2一起是 亚烷基链,R4各自独立地为卤素,烷基,烷氧基,任选取代的芳基或硝基,n为0,1,2或3,包括水解式IMAMA的1-卤代-2-芳氧基-1-烯烃, 其中Hal为氯或溴,在酸性条件下,在约20℃至150℃的温度下,直到其完全达到约95-100%,加入碱,然后使反应在弱碱性条件下在约 有利的是,反应的所有阶段在单一容器中在约40℃至100℃的温度下进行,并且在惰性有机溶剂的存在下,任选与水作为溶液的混合物或 作为两相体系,约1摩尔一元酸 每摩尔1-卤代-2-芳氧基-1-烯烃使用2摩尔碱金属碳酸盐。 最终产品是已知的杀真菌剂中间体。