A rearrangement in the reaction of αα-dichloroacetophenone with sodium methoxide

Henery-Logan, Kenneth R.; Fridinger, T. L.

doi:10.1039/c19680000130

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Cited by 6 publications

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“…(17) Preparation of a-iminoorthothiocarboxylates [181]. (18) Preparation of ortho esters by the reaction of diphenylacetylene, chloroform, and ethylene oxide at elevated temperatures in the presence of tetramethylammonium bromide [182].…”

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confidence: 99%

Ortho Esters

Sandler¹

1986

Organic Functional Group Preparations

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Section: ]mentioning

confidence: 99%

Ortho Esters

Sandler¹

1986

Organic Functional Group Preparations

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“…The functional groups found in 16 and 20, the azine of an a-keto orthoester and of its derived carboxylate ester, are to the best of our knowledge the first examples of their kind in the literature. The closest analogies to 16 are the aforementioned imidazole (18,19), ester, and carboxamate (20-24) derivatives and, in particular, a-imino ortho esters synthesized from the hydrazonium salts of pyruvaldehyde acetal (27).…”

mentioning

confidence: 99%

Structure and reactivity in highly halogenated ketazines

Lai¹,

Mackay²,

Taylor³

et al. 1988

Can. J. Chem.

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. Can. J. Chem. 66,2839Chem. 66, (1988. The azines of acetophenone and its mono-and di-chlorinated derivatives show a bathochronic shift in the yellow region, but the azine of trichloroacetophenone is colorless. Similar trends are observed in the brominated analogs and in the chlorinated propiophenone azines. The colorless tetrachloropropiophenone azine (13) is shown by X-ray analysis to be nonplanar at the azine atoms (N-N torsion angle, 126.7"). Hexachloroacetophenone azine (9) undergoes displacement of all its chlorines with NaOMe to give the hexamethoxy compound 16, also colorless. With acid, 16 gives the yellow planar (X-ray) ketazine diester 20. These reactions appear to be general for the trichloromethyl group in azines, but not for the a,a-dichloroalkyl group, attempts at the sequeice 13 to 28 proving unsuccessful.

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Sulfinate ions as nucleophiles

Okuyama

1990

Sulphinic Acids, Esters and Derivatives (1990)

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A rearrangement in the reaction of αα-dichloroacetophenone with sodium methoxide

Cited by 6 publications

References 0 publications

Ortho Esters

Ortho Esters

Structure and reactivity in highly halogenated ketazines

Sulfinate ions as nucleophiles

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