[2 + 3]‐Cycloadditions of Diazoalkanes with Imines of Hexafluoroacetone and Chloral.

Mlostoń, Grzegorz; Bodzioch, Agnieszka; Cebulska, Z.; Linden, Anthony; Hiemgartner, H.

doi:10.1002/chin.200744121

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“…In a recent paper, we described that electron-deficient imines derived from hexafluoroacetone failed to react with DMC [18]. The present study is aimed at the examination of the reactivity of imines, which are activated by a sulfonyl group attached to the N-atom, toward DMC.…”

Section: Methodsmentioning

confidence: 94%

The First Reaction of Dimethoxycarbene with an Imine Moiety

Mlostoń¹,

Heimgartner²

2007

Helvetica Chimica Acta

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The nucleophilic dimethoxycarbene (DMC; 2) generated by thermal decomposition of 2,5-dihydro-1,3,4-oxadiazole derivative 1 in boiling toluene reacts smoothly with N-(9H-fluoren-9-ylidene)-4-methylbenzenesulfonamide (7b) to yield carbonimidoate derivative 10. A multi-step reaction pathway, initiated by the attack of DMC onto the C=N bond and followed by the migration of the sulfonyl group (or via a sulfinate anion) is proposed to explain the formation of the final product. In contrast to the formal ketimine 7b, N-benzylidene-4-methylbenzenesulfonamide (7a), a formal aldimine, does not react with DMC under comparable conditions.

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Section: Methodsmentioning

confidence: 94%

The First Reaction of Dimethoxycarbene with an Imine Moiety

Mlostoń¹,

Heimgartner²

2007

Helvetica Chimica Acta

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“…10). 49 Similarly, a heterocyclic production was carried out using N-trifluoroacetylimines of trifluoropyruvate 54 in the presence of diazomethane, but a mixture of triazolines 55 and aziridines 56 was obtained (Fig. 10).…”

Section: F Meyermentioning

confidence: 99%