The Quantitative Analysis of Alkyllithium Compounds<sup>1</sup>

Gilman, Henry; Haubein, A. H.

doi:10.1021/ja01237a031

Cited by 436 publications

(126 citation statements)

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“…Upon cooling t o 0°C the adduct l b was obtained a s a yellow crystalline solid which was washed with 30 ml dry ether and taken up in 100 ml dry tetrahydrofuran. A 2 ml aliquot of the above solution was hydrolyzed with 10 m l water and the concentration determined by titration with hydrochloric acid (8). -65°C for 0.5 h, allowed to return to 25°C and stir for I .5 h after which 50 ml water was added.…”

Section: Methodsmentioning

confidence: 99%

Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Ondrus¹,

Pasutto²,

Knaus³

et al. 1978

Can. J. Chem.

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THEODORE A. ONDRUS, FRANK M. PASUTTO, EDWARD E. KNAUS, and C. S. GIAM. Can. J. Cheni. 56. 1913Cheni. 56. (1978.Reaction of the anibident I-lithio-I,2-dihydropyridines (1) and related dienaniines (2) with several electrophiles has been investigtaed. Reaction of 1 with aliphatic isocyanates occurs predominantly or exclusively at nitrogen, whereas siniilar reactions eniploying 2 do not proceed and a dinieric product 8 resulting from self condensation of 2 is obtained. In contrast, reaction of 20 with the niore electrophilic phenyl isocyanate (3c) gave both N-phe~iylaniinocarbonyl-2-11-butyl-l,2-dihydropyridine (4rl) and 2-11-butyl-5-phenylaniinocarbonylpyridine (6rl) whereas a siniilar reaction with l a afforded 4r1, Srl, and 6r1, as well as the stable N-unsubstituted-1.2-dihydropyridine 7rl. Novel 2-11-butyI-5-(2-,3-,4-pyridylcarbonyl)-I,2-dihydropyridines 130-c are obtained from reaction of lrr with pyridyl esters 120-c. Reaction of lrr with diethyl chlorophosphate and ethyl acetate occurs exclusively at nitrogen to afford high yields of 160 and 160, respectively. The mechanism for the formation of the 1,5-disubstituted-I,2-dihydropyridines S is described. THEODORE A. ONDRUS, FRANK M. PASUTTO, EDWARD E. KNAUS et C. S. GIAM. Can. J. Chem. 56, 1913Chem. 56, (1978.On a ttudit la reaction entre divers electrophiles et des lithio-l dihydro-1,2 pyridines (1) et des ditnamines (2) qui leur sont relikes et qui possedent deux sites reactifs. La reaction de 1 avec les isocyanates aliphatiques se prodirit principalernent ou exclusivement au niveau d e I'azote; des reactions semblables faisant appel i 2 ne se produisent pas et I'on obtient que le diniere 8 resultant de I'autocondensation dc 2. Par opposition, la reaction de 20 avec I'isocyanate de phenyle qui est plus electrophile (3c) conduit a la N-phenylarninocarbonyl 11-butyl-2 dihydro-1,2 pyridine (4d) ainsi qu'a de la 11-butyl-2 phenylaminocarbonyl-5 pyridine ( 6 4 ; une reaction semblable avec la l o fournit 4r1, Srl, 6d ainsi que 7r1, la dihydro-1,2 pyridine nonsubstituee sur I'azote qui est stable. On a obtenu les nouvelles rr-butyl-2(pyridylcarbonyl-2 oil -3,-4)-5 dihydro-l,2 pyridines 130-c par reaction de In avec les esters d e pyridyl 120-c. La reaction de l o avec le chlorophosphate de diethyle et I'acetate d'ethyle se produit exclusivenient au niveau de I'azote pour conduire, avec de bons rendenients, a 160 et 16b respectivenient. On decrit le mecanislne conduisant h la formation des dihydro-1,2 pyridines disubstituees en ] , 5 (5). [Traduit par le journal]

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Section: Methodsmentioning

confidence: 99%

Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Ondrus¹,

Pasutto²,

Knaus³

et al. 1978

Can. J. Chem.

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“…After washing with 30 ml of dry ether, the crystals were taken up in 100 ml of anhydrous_ tetrahydrofuran. A 2 ml aliquot of the above solution was decomposed with 10 ml of water and the concentration determined by titration with hydrochloric acid (18). Aniline (4), 2-Phenylpyridine ( 5 4 , N-Benzylaniline (6a) 2-Phenyl-5-benzylpyridine ( 7 4 , and 2-Phenyl-5-(a-anilinobenzy1)pyridine (8) General Procedure N-Benzylideneaniline (0.82 g, 0.004535 mol) in 2 ml of dry tetrahydrofuran was added dropwise with shaking to a solution of 1-lithio-2-phenyl-l,2-dihydropyridine (0.74 g, 0.004535 mol) in 10 ml of dry tetrahydrofuran under an atmosphere of nitrogen at 0".…”

Section: Methodsmentioning

confidence: 99%

Some Reactions of 1-Lithio-2-phenyl-1,2-dihydropyridine. IV. Synthesis of β-Substituted Pyridines

Giam¹,

Knaus²,

Lockhart³

et al. 1975

Can. J. Chem.

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Alkylation of the ambident anion 1-lithio-2-phenyI-1,2-dihydropyridine (1a) has been investigated. A direct method for introducing an alkyl or arylalkyl group into the β-position of pyridine is described. Reaction of 1a with styrene oxide or ethylene oxide afforded 2-(2-phenyl-5-pyridyl)-1-phenylethanol (10) and 2-(2-phenyl-5-pyridyl)ethanol (11), respectively. With N-benzylideneaniline the unexpected 2-phenyl-5-benzylpyridine (7) was obtained. When 1a was allowed to react with perhalomethanes, conditions conducive to carbene formation, bis(6-phenyl-3-pyridyl)methane (12) and 6,6′-diphenyl-3,3′-dipyridyl (13) were obtained. Mechanisms for the formation of 7, 12, and 13 are discussed. Reactions of 1a with other electrophilic substrates are described.

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“…2) The hydrosilation reaction of the polymer end SiH function (3) with allyl alcohol in the presence of platinum catalyst provided the hydroxypropyl end poly(DMS) (4).…”

mentioning

confidence: 99%

Syntheses and Reactions of Uniform Size Poly(dimethylsiloxane) with Various Reactive End Groups

Kazama

Tezuka

Imai

1987

Polym J

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ABSTRACT:The reaction of monofunctional living poly(dimethylsiloxane), poly(DMS), with dimethylchlorosilane (2), followed by the hydrosilation of the polymer end SiH group with allyl alcohol was performed. The hydroxyl end group ofpoly(DMS) (4) thus obtained was subsequently converted to the tosylate ester group through treatment with tosyl chloride in the presence of 4-dimethylaminopyridine (DMAP). The tosylate ester end group of poly(DMS) (5) was found to initiate the cationic ring opening polymerization of 2-methyl-2-oxazoline (OXZ) to produce the poly(DMS)/poly(OXZ) block copolymer (7).KEY WORDS Poly(dimethylsiloxane) I Reactive Oligomer I Block Copolymer I Poly(oxazoline)

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The Quantitative Analysis of Alkyllithium Compounds¹

Cited by 436 publications

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Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Some Reactions of 1-Lithio-2-phenyl-1,2-dihydropyridine. IV. Synthesis of β-Substituted Pyridines

Syntheses and Reactions of Uniform Size Poly(dimethylsiloxane) with Various Reactive End Groups

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The Quantitative Analysis of Alkyllithium Compounds1

Cited by 436 publications

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Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Some reactions of 2-n-butyl(phenyl)-1,2-dihydropyridines with isocyanates, pyridyl esters, and diethyl chlorophosphate

Some Reactions of 1-Lithio-2-phenyl-1,2-dihydropyridine. IV. Synthesis of β-Substituted Pyridines

Syntheses and Reactions of Uniform Size Poly(dimethylsiloxane) with Various Reactive End Groups

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The Quantitative Analysis of Alkyllithium Compounds¹