Reaction of 2-carboalkoxymethylenecyclopropanes with phenyl azide

Crandall, Jack K.; Conover, Woodrow W.; Komin, Joyce B.

doi:10.1021/jo00902a006

Cited by 23 publications

(9 citation statements)

References 3 publications

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“…Triazoles 29 are known species and the spectral data and physical properties for 29 were totally consistent with those reported previously (19,32,33).…”

Section: Resultssupporting

confidence: 89%

“…Unfortunately those were also the products when the thermolyses were done in methyl acrylate or in dimethyl acetylenedicarboxylate (DMAD), two efficient dipolarophiles (8). Heterocycles 13 and 16 were identified on the basis of the spectroscopic data, which correspond well with those oi similar known aromatic heterocycles (Table 1) (12)(13)(14)(15)(16)(17)(18)(19)(20). A significant feature of the nrnr data is that the two methyl groups that are not part of the t-Bu substituent are magnetically equivalent, providing strong evidence that the 1,2,4-triazoline ring of 12 and 15 is not present in 13 and 16.…”

Section: Resultssupporting

confidence: 54%

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The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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Treatment of 4-tert-butyl-3,3-dimethyl-5-methylene-Δ1-1,2,4-triazoline (3) with benzonitrile oxide (9), diphenylnitrile imine (10), phenyl azide, and p-nitrophenyl azide led, in each case, to 1,3-dipolar cycloaddition. The products, Δ1-1,2,4-tri-azolines that are spiro-fused to another 5-membered ring, could be isolated in pure form in three of the four cases. All four are thermally unstable and decompose by loss of N2 from the Δ1-1,2,4-triazoline moiety to form an azomethine ylide. Subsequent reactions of those ylides are described.

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“…Triazoles 29 are known species and the spectral data and physical properties for 29 were totally consistent with those reported previously (19,32,33).…”

Section: Resultssupporting

confidence: 89%

Section: Resultssupporting

confidence: 54%

The synthesis and unimolecular decomposition of four novel Δ¹-1,2,4-triazolines

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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“… a Syntheses of catalysts and diazo compounds are summarized in ESI; 15 reactions were carried out at room temperature for 72 h using [Co( P3 )] under N 2 ; isolated yields; the trans : cis diastereomeric ratios were determined by 1 H-NMR; enantiomeric excesses were determined by chiral HPLC. b [2 S ,3 R ] absolute configuration determined by anomalous-dispersion effects in X-ray diffraction measurements on a crystal.…”

Section: Resultsmentioning

confidence: 99%

Stereoselective radical C–H alkylation with acceptor/acceptor-substituted diazo reagents via Co(ii)-based metalloradical catalysis

et al. 2015

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Co(II)-based metalloradical catalysis has been, for the first time, successfully applied for asymmetric intramolecular C–H alkylation of acceptor/acceptor-substituted diazo reagents. Through the design and synthesis of a new D2-symmetric chiral amidoporphyrin as the supporting ligand, the Co(II)-based metalloradical system, which operates at room temperature, is capable of 1,5-C–H alkylation of α-methoxycarbonyl-α-diazosulfones with a broad range of electronic properties, providing the 5-membered sulfolane derivatives in high yields with excellent diastereoselectivity and enantioselectivity. In addition to complete chemoselectivity toward allylic and allenic C–H bonds, the Co(II)-based metalloradical catalysis for asymmetric C–H alkylation features a remarkable degree of functional group tolerance.

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“…Unsymmetrically carbon-substituted vic-triazoles can exist in three tautomeric forms: 1H (I), 2H (11), and 3H (111); but the 13C-NMR spectrum of Rem.…”

Section: Resultsmentioning

confidence: 99%

“…made possible by a preliminary I3C study (9) of several 1,4-and 1,5-disubstituted triazoles ( Table 11) and by comparison with values of the literature (10)(11)(12). It can be noticed that 1,4-triazoles are characterized by a difference in chemical shift between C4 and C5 (A64-5) of the order of 23-30 ppm, whereas in 1,5-disubstituted triazoles, A64-5 is comparatively small (3-10 ppm).…”

Section: Resultsmentioning

confidence: 99%