Aziridine. XV. Synthesis and reactions of 1,3-diazabicyclo[3.1.0]hex-3-enes

Heine, Harold W.; Weese, Richard H.; Cooper, Robert; Durbetaki, A. J.

doi:10.1021/jo01284a014

Cited by 55 publications

(28 citation statements)

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“…Compounds 1a,b were prepared by the method reported in [34] and compound 1c by that in [33]. Quantum-chemical calculations were made using the Gaussian 03 program package [35].…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Kadina

Новиков

Khlebnikov

et al. 2008

Chem Heterocycl Comp

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“…Compounds 1a,b were prepared by the method reported in [34] and compound 1c by that in [33]. Quantum-chemical calculations were made using the Gaussian 03 program package [35].…”

Section: Methodsmentioning

confidence: 99%

“…The dichlorocarbene was generated by basic hydrolysis of chloroform under phase transfer catalytic conditions (CHCl 3 /KOH / BnEt 3 NCl). The diazabicyclohexenes 1a-c which show interest as photochromic compounds can be readily prepared from the corresponding chalcone dibromide and ketone R 2 C(O)CH 2 R 3 in the presence of ammonia [33,34].…”

mentioning

confidence: 99%

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Kadina

Новиков

Khlebnikov

et al. 2008

Chem Heterocycl Comp

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“…A contrasting behavior is shown by the series of bicyclic aziridines which were just described by Heine and co-workers (19). 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).…”

Section: Photochromism In Bicyclic Aziridinesmentioning

confidence: 96%

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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“…Heine and co-workers found that derivatives of 3 were photochromic and behaved like 8 toward dipolarophiles upon heating (5). The irradiation of derivatives of 3 has recently been reinvestigated, and both 2 and 8 were detected among the 3The characterization of intermediates in a photochemical reaction by irradiation at low temperatures is a powerful technique for understanding the mechanism (3).…”

Section: Introductionmentioning

confidence: 99%

Electronic Excited States of the Cyclic 1,4-Diaza-1,3-diene (Cyclic α-Diimine) System. Photochemical Reactions of 2H-Isoimidazole, 5,6-Dihydropyrazine, and 1,4-Diazepine Derivatives

Arnold¹,

Abraitys²,

McLeod³

1971

Can. J. Chem.

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The five-, six-, and seven-membered cyclic 1,4-diaza-l,3-dienes have been irradiated under a variety of conditions. The six-membered ring (dihydropyrazine) opens in a 6ne valence isomerization reaction. The resulting enediimine is stable at low temperatures and has been characterized (i.r.). Irradiation of 2,3,5,5-tetramethyl-5,6-dihydropyrazine (lb) results in formation of the enediimine 26 which reacts further to give the rearranged monomer 12 and/or dimers 13 depending upon the temperature. The fiveand seven-membered systems are stable to irradiation in inert solvents. However, irradiation of 2,2-dimethyl-4,5-diphenylisoimidazole (10h) in isopropyl alcohol gives the dihydroderivative 19 and in tetramethylethylene the one-to-one adduct 25.The U.V. spectrum of the six-membered ring (5,6-dihydropyrazine) is very different from that of the five-and seven-membered rings. The long wavelength maximum (ca. 350 nm) of the six-membered ring is attributed to a transition directly into an excited state common to the enediimine 2 (i.e., the excited state has a node between C-5 and -6 of the dihydropyrazine).

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Aziridine. XV. Synthesis and reactions of 1,3-diazabicyclo[3.1.0]hex-3-enes

Cited by 55 publications

References 0 publications

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Azirino[c]imidazolyl ylides in the domino reaction of 2,2-dialkyl-4,6-diaryl-1,3-diazabicyclo[3.1.0]hex-3-enes with dichlorocarbenes. Synthesis of (1RS,5SR, 6RS)-4-(alk-1-enyl)-1,5-diaryl-3,7,7-trichloro-2,4-diazabicyclo[4.1.0]hept-2-enes

Photochemistry of Some Three-Membered Heterocycles

Electronic Excited States of the Cyclic 1,4-Diaza-1,3-diene (Cyclic α-Diimine) System. Photochemical Reactions of 2H-Isoimidazole, 5,6-Dihydropyrazine, and 1,4-Diazepine Derivatives

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