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Synlett 1997; 1997(9): 1029-1039
DOI: 10.1055/s-1997-1520
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Synthesis and Chemistry of Substituted 1-Azabicyclo[1.1.0]butanes

Romuald Bartnik1 , Alan P. Marchand2
  • 1Department of Organic and Applied Chemistry, University of Łódź, Narutowicza 68, 90-136 Łódź, Poland, FAX: 48-42-781609; E-mail: bartnik@chemul.uni.lodz.pl
  • 2Department of Chemistry, University of North Texas Denton, Texas 76203-0068, USA, FAX: (817)565-4318; E-mail: fg83@jove.acs.unt.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Methods for preparing substituted 1-azabicyclo[1.1.0]butanes are reviewed, and their potential usefulness as intermediates in organic synthesis is assessed. Particularly important synthetic applications of 1-azabicyclo[1.1.0]butanes include: (i) their use as synthons in connection with the preparation of a wide range of 3-substituted azetidines, including natural products which contain a 3-substituted azetidine moiety; (ii) the use of 1-azabicyclo[1.1.0]butane and of 3-(bromomethyl)-1-azabicyclo[1.1.0]butane as key intermediates in newly-developed syntheses of 1,3,3-trinitroazetidine (TNAZ); (iii) their use as convenient intermediates for the preparation of N,3-distubstituted 2-azetines; (iv) their use as starting reagents for the preparation of new polymeric and/or oligomeric materials.

1-azabicyclo[1.1.0]butanes - synthesis - electrophilic additions to strained C-N bonds