Mechanistic Considerations for the Consecutive Cyclization of 2,3-Dibromopropylamine Hydrobromide Giving a Strained Molecule, 1-Azabicyclo[1.1.0]butane
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- Hayashi Kazuhiko
- Faculity of Pharmaceutical Sciences, The University of Tokushima
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- Ikee Yoshifumi
- Faculity of Pharmaceutical Sciences, The University of Tokushima
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- Goto Satoru
- Faculity of Pharmaceutical Sciences, The University of Tokushima
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- Shiro Motoo
- Rigaku Corporation
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- Nagao Yoshimitsu
- Faculity of Pharmaceutical Sciences, The University of Tokushima
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Abstract
The effective formation of 1-azabicyclo[1.1.0]butane (2) by treatment of 2,3-dibromopropylamine hydrobromide (1) with n-BuLi could be understood considering a rational reaction pathway via both transition states 10 and 19 based on the intramolecular Br···Li+ coordination. A similar cyclization pathway starting from N-benzyl-3-bromopropylamine hydrochloride (17) to afford N-benzylazetidine (18) could also be postulated on the basis of a transition state 20 involving the intramolecular Br···Li+ coordination.
Journal
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- Chemical and Pharmaceutical Bulletin
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Chemical and Pharmaceutical Bulletin 52 (1), 89-94, 2004
The Pharmaceutical Society of Japan
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Details 詳細情報について
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- CRID
- 1390001204171270784
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- NII Article ID
- 110003615482
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- NII Book ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL BIB ID
- 6794912
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- PubMed
- 14709873
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed
