1,2-Di-(2-pyridyl)-ethane<sup>1,2</sup>

Campbell, Paul G.; Teague, Peyton C.

doi:10.1021/ja01634a055

Cited by 17 publications

(4 citation statements)

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“…For example, coupling has been reported by treatment of solutions of lithio 2-methylpyridine with air (1 1), oxygen ( 6 ) , bromine (12), and CuCl or CuBrz (13). Recently, it has been shown that lithio 2,6-di-tert-butyl-4-methylpyridine undergoes coupling upon treatment with iodine (14).…”

Section: Oxidative Couplingmentioning

confidence: 99%

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

Jahangir¹,

Wang²,

Smith³

et al. 1990

Can. J. Chem.

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. Can. J. Chem. 68, 587 (1990).The anion of 5-ethenyl-4-methyl-3-pyridinecarbonitrile 1 undergoes oxidative coupling on treatment with dibenzoyl peroxide affording 1,2-bis-(5'-ethenyl-3'-cyano-4'-pyridyl)-ethane, 2. It is also shown that the anions of 2-and 4-methylpyridine undergo oxidative coupling. In the latter case, however, the coupling reaction is accompanied by addition to the carbonyl group of dibenzoyl peroxide. The addition products have been identified as phenacyl pyridines and dipicolyl phenyl carbinols. The ethenyl side chain of 1 has been hydrated by way of the oxymercuration-reduction process and the secondary alcohol oxidized to a ketone. Both the alcohol and ketone in protected form are potentially useful intermediates in alkaloid synthesis.

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Section: Oxidative Couplingmentioning

confidence: 99%

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

Jahangir¹,

Wang²,

Smith³

et al. 1990

Can. J. Chem.

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“…On the other hand, only a 2% yield of 2,6-di (bromomethy1)pyridine [26] is obtained from 2,6lutidine in this way. Di-and monohalogenomethyl compounds can be prepared by reducing trihalogenomethyl compounds with tin in hydrochloric acid [lo-121 Campbell and Teague [37] assume that 2-bromomethylpyridine is an intermediate in the formation of 1,2-di(pyrid-2yl)ethane by the reaction of bromine on 2-picolyl-lithium, Barnes and Fales [26] obtained a very small yield (1 %) of 2,6-di(bromomethyl)pyridine from 2,6-lutidine with phenyllithium and bromine.…”

Section: (13mentioning

confidence: 99%

(Halogenomethyl)pyridines and (Halogenomethyl)quinolines

Mathes¹,

Schüly²

1963

Angew. Chem. Int. Ed. Engl.

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The nonspecific acid hydrolysis of proteins in aqueous solution becomes a subtratespecific reaction within layer silicates that are capable of swelling. The specificity depends, on the one hand, on the number and distribution of the negative charges in the silicate sheet, and, on the other, on the number and distribution of the c-amino-and guanido groups in the protein. Plausible menon as well [a]. Investigations with these enzyme models are, however, made difficult by the fact that they are only slightly stable in the hydronium form, and, on storage, partial decomposition into a form containing hydroxoaluminum and magnesium cations occurs [69,70].

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“…The decomposition of 2-diazobenzophenone tetrafluoroborate (1) was first carried out by Graebe and Ullman,3 who found that 1 could be converted into 9-fluorenone (4). DeTar and Relyea4 showed the formation of o-hydroxybenzophenone (3, Z = OH) along with 9-fluorenone (4) in the system, in the presence and absence of a copper catalyst. Lewin and Cohen53 then elucidated conditions under which homolytic and heterolytic cleavage of the carbon-nitrogen bond occurred.…”

mentioning

confidence: 99%

Reduction products in copper(I)-promoted diazonium ion reactions. Hydrogen abstraction from amines coordinated to copper(I), from water, and from transient radicals

Lewin¹,

Peterson²,

Michl³

1974

J. Org. Chem.

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Reduction products are observed in amine-copper(I) perchlorate promoted decomposition of aryldiazonium salts when the amine ligands are capable of hydrogen atom donation. The effective reducing agents evidently are the complexed rather than the free ligands, i.e., the tris(amine)copperd) cation in the case of tetraand tricoordinated salts and the bis(amine)copper(I) cation in the dicoordinated systems, in the presence of excess ligand a new product is obtained, which is probably an ammonium salt formed from the amine and the incipient aryl cation. In the absence of hydrogen-donating ligands it has been shown that the small but consistent amount of benzophenone formed in the copper®-promoted decomposition of 2-diazobenzophenone tetrafluoroborate arises from (a) the precursor to 9-fluorenone and (b) the solvent, water. Hydrogen atom abstraction from both these sources is rate determining and subject to a kinetic isotope effect. Since water is a notoriously poor hydrogen atom donor, transfer of a hydrogen atom from the equated coordination sphere of copper® via a bridged intermediate is postulated.

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1,2-Di-(2-pyridyl)-ethane^1,2

Cited by 17 publications

References 0 publications

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

(Halogenomethyl)pyridines and (Halogenomethyl)quinolines

Reduction products in copper(I)-promoted diazonium ion reactions. Hydrogen abstraction from amines coordinated to copper(I), from water, and from transient radicals

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1,2-Di-(2-pyridyl)-ethane1,2

Cited by 17 publications

References 0 publications

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

Oxidation products of 5-ethenyl-4-methyl-3-pyridinecarbonitrile and 2- and 4-methylpyridines

(Halogenomethyl)pyridines and (Halogenomethyl)quinolines

Reduction products in copper(I)-promoted diazonium ion reactions. Hydrogen abstraction from amines coordinated to copper(I), from water, and from transient radicals

Contact Info

Product

Resources

About

1,2-Di-(2-pyridyl)-ethane^1,2