Additions of a Phosphorane to Dimethyl Acetylenedicarboxylate

Hendrickson, James B.; Hall, Calvin; Rees, R.; Templeton, J. F.

doi:10.1021/jo01021a012

Cited by 24 publications

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“…Vycor-Filtered Photolysis of Benzhydrylidene Benzylidene Azine (12) in Methanol.-The photolysis and isolation procedures were the same as those described for the Vycor-filtered irradiation of 1 except that 3.00 mmol of benzhydrylidene benzylidene azine16 (14) were irradiated. No single product could be isolated in sufficient quantity for identification; in particular, no benzonitrile, benzophenone, or benzaldehyde were isolated.…”

Section: Methodsmentioning

confidence: 99%

“…Of these five photoproducts, The former of these two possibilities is in best agreement with experimental observation. The first fact relating to this question is that in the photolysis of benzhydrylidene benzylidene azine (12), where a 12 2 + 3 + 6 three (2, 3, and 6) had been obtained and identified in the irradiation of benzophenone azine (1). The remaining two (10 and 11) were assigned structures after comparison with independently obtained samples.…”

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Photochemistry of unsaturated nitrogen-containing compounds. VIII. Photochemistry of benzophenone azine

Gorse¹,

Binkley²

1972

J. Org. Chem.

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Benzophenone azine (1) has been found to be the beginning point for two different types of photochemical reaction. The first of these is a molecular rearrangement leading to 1,3,3-triphenylisoindole (5) while the second is a photoreduction resulting in the formation of 1,1,1',!'-tetraphenylazomethane (7). l,l,l',l'-Tetraphenylazomethane (7) has also been found to be photochemically unstable yielding 1,1,2,2-tetraphenylethane (2) and diphenylmethane (3). 1,1,2,2-Tetraphenylethane (2) has been previously shown to decompose upon photolysis to give cfs-stilbene (4), l-(2-biphenylyl)-l,2-diphenylethane (6), and biphenyl (8). All of these compounds (2-8) are isolated from the photolysis of benzophenone azine (1).Benzophenone azine (1) has been found to be photochemically unique among azine systems. It does not participate in nitrogen-nitrogen bond homolysis, the major light-initiated reaction experienced by other acyclic azines.3 It does, however, undergo two reac-^)C=NN=C^^) C=N• -N=Ct ions, a photoreduction and a molecular rearrangement.At this time we would like to describe our findings related to these two photochemical reactions of benzophenone azine (1). ResultsVycor-filtered irradiation of 3.00 mmol of benzophenone azine (1) in 1200 ml of methanol under nitrogen for 24 hr with a 450-W Hanovia mercury-vapor lamp produced, after solvent removal, a dark yellow oil containing some solid material. Chromatography (1) Paper VIII in a series on the photochemistry of unsaturated nitrogencontaining compounds. For paper VII see R. W.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Photochemistry of unsaturated nitrogen-containing compounds. VIII. Photochemistry of benzophenone azine

Gorse¹,

Binkley²

1972

J. Org. Chem.

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“…The benzothiazole derivative(74) can be desulfurized with Raney nickel to give the dihydropyridine derivative(75). 2-AIkyl derivatives of benzothiazole also add two moles of the ester to form the azepine derivatives(76), which can be desulfurized with Raney nickel to give (77).…”

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Additions to the Activated CC Triple Bond

Winterfeldt

1967

Angew. Chem. Int. Ed. Engl.

108

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The possibilities of additions to the activated CC triple bond are discussed with the aid of a number of examples. The additions of donors that contain no active hydrogen are generally initiated via a dipolar primary complex, which can undergo stabilization by rearrangement, cyclization, or addition reactions. Preparative aspects of these reactions are also discussed. They offer routes for the preparation of heterocycles, particularly pyrrole and thiophene derivatives.

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Cycloadducts from Diazocumulenes and 1,2,3(λ3)-Diazaphospholes: Thermolysis Generates Products Derived from 3-Alkenylidene-1,2,3(λ5)-diazaphospholes

Kerth

Maas

1999

Eur. J. Org. Chem.

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Additions of a Phosphorane to Dimethyl Acetylenedicarboxylate

Cited by 24 publications

References 0 publications

Photochemistry of unsaturated nitrogen-containing compounds. VIII. Photochemistry of benzophenone azine

Photochemistry of unsaturated nitrogen-containing compounds. VIII. Photochemistry of benzophenone azine

Additions to the Activated CC Triple Bond

Cycloadducts from Diazocumulenes and 1,2,3(λ3)-Diazaphospholes: Thermolysis Generates Products Derived from 3-Alkenylidene-1,2,3(λ5)-diazaphospholes

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