The photochemistry of acetylenic ethers. A novel carbon-oxygen to carbon-carbon bond conversion

Smith, Bradley A.; Callinan, A.; Swenton, John S.

doi:10.1016/0040-4039(94)85199-9

Tetrahedron Letters

1994

DOI: 10.1016/0040-4039(94)85199-9

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The photochemistry of acetylenic ethers. A novel carbon-oxygen to carbon-carbon bond conversion

Bradley A. Smith

A. Callinan

John S. Swenton

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Cited by 4 publications

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“…The acetalic products 6 are obtained in one pot from 5 , after elimination with 1 equiv of base. To assess the best reaction conditions, 5 was initially reacted with ethylene glycol 4a using different tert -butanolate salts, as suggested in the literature …”

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confidence: 99%

Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

et al. 2007

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confidence: 99%

Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

et al. 2007

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ChemInform Abstract: The Photochemistry of Acetylenic Ethers. A Novel Carbon‐Oxygen to Carbon‐Carbon Bond Conversion.

1994

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Photochemistry of Diethynyl Sulfides: A Cycloaromatization for the Formation of Five-Membered Rings

2003

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The first five-membered ring cycloaromatization reaction has been demonstrated. Photoirradiation of bis(phenylethynyl) sulfide in hexanes/1,4-cyclohexadiene produces 3,4-diphenylthiophene through the presumed intermediacy of 2,5-didehydrothiophene. In addition, phenylacetylene is produced in this reaction consistent with competing direct carbon-sulfur cleavage. For reactions in ethanol or 2-propanol production of the thiophene is accompanied by the formation of phenylacetylene and a thionoester of the corresponding alcohol. Thiophene products also result from the irradiation of other diethynyl sulfides. [reaction: see text]

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The photochemistry of acetylenic ethers. A novel carbon-oxygen to carbon-carbon bond conversion

Cited by 4 publications

References 14 publications

Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

Chiral Polycyclic Ketones via Desymmetrization of Dihaloolefins

ChemInform Abstract: The Photochemistry of Acetylenic Ethers. A Novel Carbon‐Oxygen to Carbon‐Carbon Bond Conversion.

Photochemistry of Diethynyl Sulfides: A Cycloaromatization for the Formation of Five-Membered Rings

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