Generation and synthetic applications of (3-pyridinylchloromethyl)lithium

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4148-4150

  Florio, Saverio ^a   Troisi, Luigino ^b  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000895851     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952084d     Document Type: Article

References (35)

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30. (3-Pyridinylchloromethyl)lithium (1b) actually has to be considered an α-halocarbanion, whereas (2-pyridinylchloromethyl)lithium (See ref 11) has a large character of an aza-enolate as suggested by spectroscopic data reported for similar species: Hogen-Esch, T. E.; Jenkins, W. L. J. Am. Chem. Soc. 1981, 103, 3666.
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32. We isolated just one isomer, and the small coupling constant between the epoxy ring hydrogens seems to suggest the trans configuration, as in similar cases. See: Florio, S., Ingrosso, G., Ronzini, L., Epifani, E. Tetrahedron 1991, 47, 3365.
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35. We isolated just one isomer, and the small coupling constant between the aziridinyl hydrogens seems to suggest the E configuration, as observed in the case of formyl aziridines: Wartski L. Bull. Soc. Chim. Fr. 1975, 1663.