Photochemical transformations of small-ring heterocyclic compounds. XXIV. Photoisomerization of the triphenyl-1,3-diazabicyclo[3.1.0]hex-3-ene system

Padwa, Albert; Clough, Stuart C.; Glazer, Edward

doi:10.1021/ja00709a070

Cited by 36 publications

(9 citation statements)

References 2 publications

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“…9 Coupling constants and NOE measurements (irradiation of HC-2 gives rise only to enhancement of HC-6) provided exhaustive information on the exo-stereochemistry of the process.…”

Section: Methodsmentioning

confidence: 99%

A Novel Efficient Three-Component One-Pot Synthesis of 1,3-Diazabicyclo[3.1.0]hex-3-ene System under Microwave Irradiation

Risitano¹,

Grassi²,

Foti³

et al. 2005

Synlett

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“…9 Coupling constants and NOE measurements (irradiation of HC-2 gives rise only to enhancement of HC-6) provided exhaustive information on the exo-stereochemistry of the process.…”

Section: Methodsmentioning

confidence: 99%

A Novel Efficient Three-Component One-Pot Synthesis of 1,3-Diazabicyclo[3.1.0]hex-3-ene System under Microwave Irradiation

Risitano¹,

Grassi²,

Foti³

et al. 2005

Synlett

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“…In solution, the lifetime of the colored intermediates was much shorter (several minutes at room temperature) and their formation was not entirely reversible due to a competing enediimine formation (12,23). In an earlier report (12), we had shown that the enediimine was formed via transient colored intermediates which were 1,3-dipoles (azomethine ylides).…”

Section: Photochromism In Mono-cyclic Aziridinesmentioning

confidence: 98%

Photochemistry of some three-membered heterocycles

Trozzolo¹,

Leslie²,

Sarpotdar³

et al. 1979

Pure and Applied Chemistry

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-The solid-state photolysis of oxiranes and aziridines produces highly colared ylide intermediates. The stability of these intermediates is dependent an a combination of electronic and steric factors as well as the solid-state constraints of the environment.Flash photolysis studies indicate that two different ylides can be produced in solution at room temperature. These intermediates appear to be identical to those formed consecutively in the solid state or lowtemperature glasses. By the use of certain gas-solid reactions, it is possible to control the lifetime of the intermediate so that it is destroyed immediately or continues to exist almest indefinitely. INTRODUCTIONThe room temperature photolyses of aryloxiranes have been shown by Griffin and co-workers to involve a two-bond cleavage producing aryl carbenes and carbonyl compounds (3,4). On the other hand, the thermal transformations of aryl aziridines were interpreted by Reine (5) and Huisgen (6) as one-bond cleavages producing azomethine ylide intermediates which could be trapped with suitable dipolarophiles.Our previous interest in low temperature and solid-state photochemical techniques (7-9) suggested the possibility of obtaining direct physical evidence for the above intermediates an photoreactions carried out at 77°K. The results of several of these studies already have appeared (10-13) and this report will describe additional recent werk with special emphasis an the relation of the low-temperature studies to the unusual room•temperature solid-state photochemistry which is exhibited by many of the compounds. LOW TEMPERATURE PHOTOCHEMISTRY OF ARYL OXIRANESThe room temperature photochemistry of aryloxiranes has been studied extensively by Griffin and co-workers (3,4). The reactions involve a cycloelimination an photolysis in solution to give aryl carbenes and carbonyl compounds. H /H~ )c=otC , - Further reactions Ar ~Ar 261Unauthenticated Download Date | 5/9/18 9:17 PM

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“…Typical of the compounds which were investigated (Table II) In solution, the lifetime of the colored intermediates was much shorter (several minutes at room temperature) and their formation was not entirely reversible due to a competing enediimine formation (12,23). In an earlier report (12), we had shown that the enediinine was formed via transient colored intermediates which were 1,3-dipoles (azomethine ylides).…”

Section: Photochromism In Bicyclic Aziridinesmentioning

confidence: 99%

Photochemistry of Some Three-Membered Heterocycles

Trozzolo¹,

Leslie²,

Sarpotdar³

et al. 1979

Photochemistry–7

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-The solid-state photolysis of oxiranes and aziridines produces highly colored ylide intermediates. The stability of these intermediates is dependent on a combination of electronic and steric factors as well as the solid-state constraints of the environment. _____ yX\Flash photolysis studies indicate that two different ylides can be produced in solution at room temperature. These intermediates appear to be identical to those formed consecutively in the solid state or lowtemperature glasses. By the use of certain gas-solid reactions, it is possible to control the lifetime of the intermediate so that it is destroyed immediately or continues to exist almost indefinitely. INTRODUCTIONThe room temperature photolyses of aryloxiranes have been shown by Griffin and co-workers to involve a two-bond cleavage producing aryl carbenes and carbonyl compounds (3,4). On the other hand, the thermal transformations of aryl aziridines were interpreted by Heine (5) and Huisgen (6) as one-bond cleavages producing azomethine ylide intermediates which could be trapped with suitable dipolarophiles.Our previous interest in low temperature and solid-state photochemical techniques (7-9) suggested the possibility of obtaining direct physical evidence for the above intermediates on photoreactions carried out at 77°K. The results of several of these studies already have appeared (10-13) and this report will describe additional recent work with special emphasis on the relation of the low-temperature studies to the unusual rooim-temperature solid-state photochemistry which is exhibited by many of the compounds. LOW TEMPERATURE PHOTOCHEMISTRY OF ARYL OXIRANESThe room temperature photochemistry of aryloxiranes has been studied extensively by Griffin and co-workers (3,4). The reactions involve a cycloelimination on photolysis in solution to give aryl carbenes and carbonyl compounds.

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Photochemical transformations of small-ring heterocyclic compounds. XXIV. Photoisomerization of the triphenyl-1,3-diazabicyclo[3.1.0]hex-3-ene system

Abstract: 5 ) All the calculations used an average C plus S f-curve for the two disordered ring atoms.(6) The crystal structure of histidine was refined by J. Donohue and A. Caron, Acta Crystallogr., 17, 1178 (1964), but the conformation about the C-C bond is given in ref 3.(7)

Cited by 36 publications

References 2 publications

A Novel Efficient Three-Component One-Pot Synthesis of 1,3-Diazabicyclo[3.1.0]hex-3-ene System under Microwave Irradiation

A Novel Efficient Three-Component One-Pot Synthesis of 1,3-Diazabicyclo[3.1.0]hex-3-ene System under Microwave Irradiation

Photochemistry of some three-membered heterocycles

Photochemistry of Some Three-Membered Heterocycles

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