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Synlett 2001; 2001(2): 0202-0205
DOI: 10.1055/s-2001-10789
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Neighbouring Group Participation in N-Methoxymethyl 7-Azanorbornanes 1: The Synthesis of N,N′-Methano-bridged Diazasesquinorbornanes, N3-[3]Polynorbornanes and CN3-[4]Polynorbornanes

Ronald N. Warrener* , Davor Margetic, Douglas N. Butler, Guangxing Sun
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia; Fax 61 7 4930 9917; E-mail: r.warrener§cqu.edu.au
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Publication History

Publication Date:
31 December 2001 (online)

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A new tandem route to N,N′-methano-bridged diazasesquinorbornanes is reported in which 7-azabenzonorbornadienes are reacted with ester-activated N-(methoxymethyl)aziridinocyclobutanes to form adducts which immediately undergo N,N′-methanobridge formation by nucleophilic attack of the nitrogen lone pair of one N-bridge onto the methoxymethyl group attached to the adjacent N-bridge. Alternative routes to N,N′-methano-bridged structures of this type are discussed.

neighbouring-group - cycloadditions - bicyclic compounds - stereoselectivity

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