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1.
A one-pot procedure for the conversion of mono-substituted arenes and heteroarenes into the ortho-cyano derivatives was achieved through directed lithiation followed by electrophilic cyanation with phenyl cyanate. This reaction method proved to be applicable to halogen-lithium exchanged intermediates, so especially useful for the synthesis of benzonitriles. The scope of the reaction sequence was explored using a number of substrates. 相似文献
2.
3.
1-(2-Methoxyethoxy)-2-methylbenzene and 1-(2-dimethylaminoethoxy)-2-methylbenzene have been lithiated using sec-BuLi under a variety of conditions and the laterally lithiated species trapped with electrophiles. 相似文献
4.
Rosario Torregrosa 《Tetrahedron》2005,61(47):11148-11155
2-Lithioimidazole was prepared by means of a new protocol, which consists of a slight excess of lithium metal in the presence of a substoichiometric amount of isoprene (20 mol%) in THF at room temperature. By reacting this organolithium with carbonyl electrophiles 2-(hydroxyalkyl)imidazoles 3 were obtained, in good yields. As a result of the reaction of the mentioned lithium intermediate with imines 4, the corresponding 2-(aminoalkyl)imidazoles 5 were isolated in excellent yields. 相似文献
5.
Recent advances in the generation of dilithiated synthons by arene-catalyzed lithiation of the corresponding dichloro compounds in the presence of carbonyl compounds (Barbier-type reaction conditions) as the key step are described. Further cyclization of the generated diols under different reaction conditions affords a variety of mono-, bi-, and spirocyclic ethers. 相似文献
6.
The reaction of 1,3-dicloro-2-butene (1; 5:1 Z:E-mixture) with lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 1% molar) in the presence of different electrophiles [EtCHO, PriCHO, ButCHO, c-C6H11CHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, (c-C3H5)2CO, Me3SiCl] in THF at temperatures ranging between −78 and −50°C gives, after hydrolysis with water, the corresponding products 2 in different Z:E-ratios depending on the electrophile used. Treatment of some diols 2 with hydrochloric acid gives dienic alcohols 3 or substituted dihydropyrans 4, depending on the structure of the starting diol. Finally, the same dichlorinated starting material is transformed into the corresponding allylic amines derived from morpholine and benzyl methyl amine and submitted to the same DTBB-catalysed lithiation as above, so after reaction with different electrophiles [ButCHO, c-C6H11CHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, Me3SiCl] and final hydrolysis with water, compounds 7 are isolated having a Z-configuration. A mechanistic explanation for this behaviour is given. 相似文献
7.
《Tetrahedron》2004,60(21):4655-4662
The lithiation of 1H,3H-benzo[de]isochromene (6) with lithium and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at −50 °C gives dianionic intermediate 7, which by reaction with different electrophiles {H2O, D2O, tBuCHO, PhCHO, Me2CO, (CH3CH2)2CO, [CH3(CH2)4]2CO, (CH2)5CO, (CH2)7CO, (−)-menthone} at the same temperature followed by hydrolysis leads to functionalised alcohols 8. If after addition of a carbonyl compound as the first electrophile [tBuCHO, (CH2)5CO, (−)-menthone], the resulting dialcoholate 9 is allowed to react at 0 °C, a second lithiation takes place to give intermediate 10 which by reaction with a second electrophile [H2O, tBuCHO, (CH2)5CO, CO2], yields, after hydrolysis, 1,8-difunctionalised naphthalenes 11. Cyclization under acidic conditions of diols 8e-i gives oxygen-containing eight-membered heterocycles, which are homologous to the starting material 6. 相似文献
8.
Katsuhiko Tomooka Nobuyuki Komine Tomoya Sasaki Hideo Shimizu Takeshi Nakai 《Tetrahedron letters》1998,39(52):2362-9718
Treatment of (E)-6-phenyl-5-hexenyl carbamates with s-BuLi/(−)-sparteine is shown to afford the trans-1,2-disubstituted cyclopentane derivatives in high % ee, along with the bicyclo[3.1.0]hexanes (bicyclization products). 相似文献
9.
The 4,4′di-tert-butylbiphenyl (DTBB)-catalysed lithiation of dihydrodibenzothiepine (1) at −78 °C for 30 min followed by reaction with a carbonyl compound [tBuCHO, Ph(CH2)2CHO, PhCHO, (n-C5H11)2CO, (CH2)5CO, (CH2)7CO, (−)-menthone] at the same temperature leads, after hydrolysis with 3 M hydrochloric acid, to sulphanyl alcohols 2. If after addition of a carbonyl compound as the first electrophile [Me2CO, (CH2)5CO, (−)-menthone], the resulting dianion of type II is allowed to react at room temperature for 30 min, a second lithiation takes place to give an intermediate of type III, which by reaction with a second electrophile [Me2CO, Et2CO, (CH2)5CO, ClCO2Et], yields, after hydrolysis, difunctionalised byphenyls 4. The cyclisation of the sulphanyl alcohol 2c under acidic conditions yields the eight-membered sulphur containing heterocycle 3. The lithiation of dihydrodinaphthoheteroepines 7 and 10 with 2.2 equiv of lithium naphthalenide in THF at −78 °C followed by reaction with different electrophiles [H2O, D2O, tBuCHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO] at the same temperature leads, after hydrolysis, to unsymmetrically 2,2′-disubstituted binaphthyls 9 and 12, respectively. When the lithiation is performed with an excess of lithium in the presence of a catalytic amount of DTBB (10% molar), a double reductive cleavage takes place to give the dianionic intermediate VII, which by reaction with different electrophiles [H2O, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO], followed by hydrolysis with water, yields symmetrically 2,2′-disubstituted binaphthyls 8 and 11. In the case of starting from (R)- or (S)-dihydrodinaphthoheteroepines 7 and 10, these methodologies allow us to prepare enantiomerically pure compounds 8, 11 and 12. 相似文献
10.
A new method has been developed for the generation and subsequent reaction of ynolates in a micro flow reactor system. This new procedure allowed for ynolates to be prepared at 0 °C or ambient temperature within 1 min via a reductive lithiation reaction, whereas the corresponding batch processes generally require low temperature control and extended reaction times of up to 1 h. The resulting ynolates were applied to the olefination of carbonyl compounds, with the reactions reaching completion in a much shorter reaction time in the continuous flow reactor than the batch reactor. These results highlight the practical utility of the ynolate reaction, and represent the first reported example of the use of lithium naphthalenide in a flow microreactor, which would contribute to progress of the flash chemistry. 相似文献