[3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage

Gaebert C, Mattay J (1997)
Tetrahedron 53(42): 14297-14316.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Under PET conditions (photoinduced electron transfer) aziridines react with dipolarophiles in a [3+2] cycloaddition to form five-membered heterocycles. In this study we, used mono- and disubstituted N-alkyl and N-arylaziridines. We noticed that the radical cation as intermediate reacts in a different manner to the classical azomethine ylide. Furthermore, under mild thermal conditions, aziridines react in acetonitrile in a formal [3+2] cycloaddition with activated acetylene derivatives under C-N bond cleavage. Using methanol as solvent, the intermediate is trapped leading to highly substituted enamines. A mechanism for this unexpected thermal reaction is proposed. (C) 1997 Elsevier Science Ltd.
Erscheinungsjahr
Zeitschriftentitel
Tetrahedron
Band
53
Zeitschriftennummer
42
Seite
14297-14316
ISSN
PUB-ID

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Gaebert C, Mattay J. [3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage. Tetrahedron. 1997;53(42):14297-14316.
Gaebert, C., & Mattay, J. (1997). [3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage. Tetrahedron, 53(42), 14297-14316. doi:10.1016/S0040-4020(97)00951-4
Gaebert, C., and Mattay, J. (1997). [3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage. Tetrahedron 53, 14297-14316.
Gaebert, C., & Mattay, J., 1997. [3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage. Tetrahedron, 53(42), p 14297-14316.
C. Gaebert and J. Mattay, “[3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage”, Tetrahedron, vol. 53, 1997, pp. 14297-14316.
Gaebert, C., Mattay, J.: [3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage. Tetrahedron. 53, 14297-14316 (1997).
Gaebert, C, and Mattay, Jochen. “[3+2] cycloadditions and nucleophilic additions of aziridines under C-C and C-N bond cleavage”. Tetrahedron 53.42 (1997): 14297-14316.