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The Products of Vicarious Nucleophilic Substitution and Annelation in the Reactions of α-Haloalkyl Carbanions with Benzonaphthyridines and their N-Oxides

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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary.

 Carbanions of chloromethyl 4-tolylsulfone, bromo- and chloromethanesulfomorpholide, and neopentyl chloromethanesulfonate react with benzonaphthyridines and their N-oxides via two pathways: vicarious nucleophilic substitution of hydrogen and annelation. The results are rationalized in terms of the negative charge delocalization in the intermediate σ-adducts.

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Authors and Affiliations

  1. Institute of Chemistry, Pedagogical University, PL-42201 Częstochowa, Poland E-mail: b.bachowska@wsp.czest.pl, , , , , , PL

    Barbara Bachowska

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  1. Barbara Bachowska
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Received October 15, 2001. Accepted (revised) November 26, 2001

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Bachowska, B. The Products of Vicarious Nucleophilic Substitution and Annelation in the Reactions of α-Haloalkyl Carbanions with Benzonaphthyridines and their N-Oxides. Monatshefte fuer Chemie 133, 1071–1076 (2002). https://doi.org/10.1007/s007060200076

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  • DOI: https://doi.org/10.1007/s007060200076

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