3017-67-2Relevant academic research and scientific papers
Pd-Catalyzed Difluoromethylation of Vinyl Bromides, Triflates, Tosylates, and Nonaflates
Chang, Dalu,Gu, Yang,Shen, Qilong
supporting information, p. 6074 - 6078 (2015/04/14)
Pd-catalyzed difluoromethylation of di-, tri- or tetra-substituted vinyl bromides, triflates, tosylates and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes. Vinyl fantasy: Pd-catalyzed difluoromethylation of di-, tri-, or tetra-substituted vinyl bromides, triflates, tosylates, and nonaflates under mild conditions is described. The reaction tolerates a wide range of functional groups, such as bromide, chloride, fluoride, ester, amine, nitrile, and protected carbonyl, thus providing a general route for the preparation of difluoromethylated alkenes.
Simple, chemoselective, catalytic olefin isomerization
Crossley, Steven W. M.,Barabé, Francis,Shenvi, Ryan A.
supporting information, p. 16788 - 16791 (2015/01/09)
Catalytic amounts of Co(SaltBu,tBu)Cl and organosilane irreversibly isomerize terminal alkenes by one position. The same catalysts effect cycloisomerization of dienes and retrocycloisomerization of strained rings. Strong Lewis bases like amines and imidazoles, and labile functionalities like epoxides, are tolerated.
Metal-free regioselective hydrobromination of alkynes through CH/CBr activation
Chen, Xiuling,Chen, Tieqiao,Xiang, Yuqiang,Zhou, Yongbo,Han, Daoqing,Han, Li-Biao,Yin, Shuang-Feng
supporting information, p. 4572 - 4575 (2014/12/10)
A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ 'HBr' source. This protocol also represents an elegant example of the activation of sp2 CH and CBr bonds in one pot, in which 'HBr' is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed.
Method to inhibit ethylene responses in plants
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Page/Page column 21; 23, (2010/02/11)
The present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein: 1) at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring, or 2) . a substituent contains silicon, sulfur, phosphorous, or boron, or 3) least one substituent contains from one to four non-hydrogen atoms and at least one substituent contains more than four non-hydrogen atoms.
Neighbouring-group influence on the ring opening of some 2-alkyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
Sydnes, Leiv K.,Alnes, Karl F. S.,Erdogan, Natalia
, p. 1737 - 1749 (2007/10/03)
Several 2-alkyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions. Ring opening gave mixtures of the corresponding acetylenic diethyl ketals and acetals. When the steric bulk of the alkyl substituent was increased acetal formation dominated, and in the case of 1,1,2-tribromo-2-(tert-butyl)cyclopropane, the acetal was formed as the only product. Springer-Verlag 2005.
Transition metal-catalyzed synthesis and reactivity of N-alkenyl aziridines
Dalili, Shadi,Yudin, Andrei K.
, p. 1161 - 1164 (2007/10/03)
(Chemical Equation Presented) Straightforward methods for palladium-catalyzed alkenylation of aziridines with alkenyl halides and copper-catalyzed alkenylation of aziridines with alkenyl boronic acids have been developed. This methodology offers attractive alternatives to the known methods requiring activated alkenyl halides and acetylenes. A wide variety of N-alkenyl aziridines containing substituents other than electron-withdrawing substituants such as cyano groups and sulfones have been synthesized in good yields. Furthermore, these N-alkenyl aziridines exhibit quite a different reactivity from conventional enamines, as demonstrated by their reactivity.
Structure based interference with insect behaviour - Cyclopropene analogues of pheromones containing Z-alkenes
Al Dulayymi, Juma'a R.,Baird, Mark S.,Simpson, Michael J.,Nyman, Susan,Port, Gordon R.
, p. 12509 - 12520 (2007/10/03)
Analogues of the pheromones of three insect species (Musca domestica L., Plutella xylostella L. and Ephestia elutella Hbn.) in which a Z-alkene has been replaced by a 1,2-disubstituted cyclopropene have been synthesized. The analogues interfere with normal mating behaviour for each species.
Structure-Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori
Ando, Tetsu,Ohno, Ryuta,Ikemoto, Kazuhisa,Yamamoto, Masanobu
, p. 3350 - 3354 (2007/10/03)
According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C16 chain and the 11,12-position in a C14 or C18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E, 12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 μg/gland, but other compounds at 1 μg/gland inhibited the conversion of [16,16,16-2H3]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C16 chain was the strongest (I50 = 0.016 μg/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-14C]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the Δ11-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Δ10,-12-desaturation by 11,12- and 13,14-methylene compounds.
Synthesis of 1,1-Disubstituted Ethenes by Means of Sequential Cross-Coupling Reactions
Fiandanese, V.,Marchese, G.,Naso, F.,Ronzini, L.
, p. 1034 - 1036 (2007/10/02)
A variety of 1-alkenes are synthesized in 63-91percent yields by means of sequential cross-coupling reactions of Grignard reagents with readily available or commercial starting materials, in the presence of transition-metal catalysts.
ORGANIC SYNTHESIS USING HALOBORATION REACTION. I. A SIMPLE AND SELECTIVE SYNTHESIS OF 2-BROMO- AND 2-IODO-1-ALKENES
Hara, Shoji,Dojo, Hidetaka,Takinami, Satoru,Suzuki, Akira
, p. 731 - 734 (2007/10/02)
B-bromo- or B-iodo-9-borabicyclononane reacts readily with 1-alkynes.Such haloboration reactions proceed through the Markovnikov addition of the X-B moiety to CC bonds and cis fashion.The bromoboration reaction occours chemoselectively at terminal CC bonds but not at internal CC, terminal and internal C=C bonds.The protonolysis of haloboration products with acetic acid gives corresponding 2-bromo- or 2-iodo-1-alkenes in excellent yields.
