Thermal intramolecular reactions of Δ<sup>1</sup>-1,2,4-triazolines with extended exocyclic unsaturation

Schwan, Adrian L.; Warkentin, John

doi:10.1139/v88-067

Cited by 3 publications

(2 citation statements)

References 9 publications

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“…Whereas the background regarding the thermolysis chemistry of A1-1,2,4-triazolines is limited to that from this laboratory (5)(6)(7)27), very much is known about N2 loss from A2-1,2,3-triazolines (28,29). Those triazolines are known to decompose via a zwitterion, rather than an ylide, to give aziridines via ring closure and (or) imino species by means of an alkyl group shift (Scheme 2 …”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

“…A [1,4]-hydrogen shift leads to A2-1 ,2,3-triazolines 27. This sigmatropic rearrangement is a known reaction of azomethine ylides (6,27,38,39). 1,2,3-Triazoline 27a deaminates to 29a upon chromatography.…”

Section: Resultsmentioning

confidence: 99%

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

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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Thermolyse von 5‐Alkyliden‐1,4‐dihydro‐5H‐tetrazolen

1990

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Pyrimidine, 3,4,5,6-tetrahydro-4-methylimino-/ Thermolysis Thermolysis of 5-Alkylidene-1,4-dihydro-5If-tetrazolesIn benzene solution at lOO"C, the isopropylidenedihydrotetrazole 1 a decomposes mainly (80%) into molecular nitrogen and the aziridinimines (E)-and (Z)-2a which are thermally unstable and afford methyl isocyanide and the imine 3a. In addition, the novel spirocyclic tetrahydropyrimidine 7a is formed (18% Uberwiegen der (E)-Diastereomeren ist nur durch konfigurativ stabile Diradikal-Zwischenstufen zu interpretieren'). Wir berichten hier iiber die Thermolyse der 5-Alkylidendihydrotetrazole 1. Dabei entstehen neben den erwarteten Aziridiniminen 2 uberraschende, neuartige Produkte (7), die entgegen friiheren Annahmen3) nicht durch primare [3 -t 21-Cycloreversion von 1 in Methylazid und Ketenimine 4 resultieren.la: R' = R2 = Me; l b R' = H, R ' = tBu; alle Produkte von l a sind mit a, die von 1 b rnit b gekennzeichnet.

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