Dianion mediated cycloreversions. A novel pyrimidinedione to pyridone conversion

Comber, Rob; Swenton, John S.; Wexler, Allan

doi:10.1021/ja00512a049

Cited by 12 publications

(2 citation statements)

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“…[98][99][100] In the course of our study of the substituent effect on this reaction, we disclosed the exceptionally facile ring opening reaction of cyclobutenes, facilitated by arylsulfinyl, arylsulfonyl, and diphenylphosphinyl carbanion. 101,102) The systems chosen for study were the (arylsulfinyl), (arylsulfonyl), and (diphenylphosphinyl)methylcyclobutenes, dienes generated from them constituting an essential part of the skeleton of the vitamin D series.…”

Section: Novel Reaction Mode and Substituent Effectmentioning

confidence: 99%

Synthetic Organic Chemistry Based on Small Ring Compounds

Nemoto

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Novel Reaction Mode and Substituent Effectmentioning

confidence: 99%

Synthetic Organic Chemistry Based on Small Ring Compounds

Nemoto

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Thymine photodimerization has been subjected to extensive studies as the dimers account for most of photobiological effects observed upon UV irradiation of cells [1,2], Dimers are not the only cyclobutane-type products of thymine. Simple alkenes, vinyl esters and ethers [1], alkynes [3], acetylenic esters [4], coumarins and psoralens [5] when undergo photoaddition to pyrimidines give cyclobutanes as well.…”

Section: Introductionmentioning

confidence: 99%

The Photoreactions of Thymine with Hypoxanthine and Imidazole

Wenska

1985

Zeitschrift Für Naturforschung B

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Photochemical reactions of thymine linked to hypoxanthine or imidazole by a trimethylene chain were studied in aqueous solution. Irradiation (λ = 254 nm) of thymine-hypoxanthine pair yielded two internal cycloadducts with azetidine and cyclobutane part structures. Sensitization and quenching experiments suggested that the excited singlet was the reactive state in the photo-cycloaddition reactions. Only cyclobutanes were isolated from irradiated (λ = 290 nm) solutions of thymine-imidazole pairs. Photocycloadditions were reversible upon irradiation at λ = 254 nm

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Anion‐Assisted Sigmatropic Rearrangements

Wilson

1993

Organic Reactions

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The use of sigmatropic rearrangements for the synthesis of organic compounds has become one of the important synthetic tools available to the organic chemist, especially since the development of the detailed stereochemical understanding of these processes in terms of orbital symmetry. The flexibility and predictability of the Cope rearrangement make this type of process widely applicable. The interest and synthetic activity related to the Cope rearrangement can be seen in a previous review of the Claisen and Cope rearrangements. In that review, several variations of the rearrangement were discussed, including examples of the “oxy‐Cope” rearrangement. In 1975 examples of an oxy‐Cope rearrangement were reported wherein an enormous rate acceleration (10 15 ) was observed on formation of the potassium salt of the oxy‐Cope substrate. This chapter surveys extensions of this type of anionic substituent effect to other [3,3]‐, [5,5]‐, [1,3]‐, and [1,5]‐sigmatropic rearrangements as well as retro‐[2 + 2] and reverse Diels–Alder reactions. Specifically excluded are the ester enolate Claisen rearrangement which is mechanistically unrelated, the Wittig rearrangement, and the Haller–Bauer reaction. The chemical literature has been searched to the end of 1989. Emphasis is placed on reactions of synthetic utility, novelty, and generality.

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Dianion mediated cycloreversions. A novel pyrimidinedione to pyridone conversion

Cited by 12 publications

References 0 publications

Synthetic Organic Chemistry Based on Small Ring Compounds

Synthetic Organic Chemistry Based on Small Ring Compounds

The Photoreactions of Thymine with Hypoxanthine and Imidazole

Anion‐Assisted Sigmatropic Rearrangements

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