Catalytic synthesis of azeheterocycles from organic azides.

One electron oxidation of bicyclic cyclopropanol, bicyclo[4.1.0]heptan-1-ol by a catalytic amount of Mn(III) promotes ring-expansion to afford 7-membered-ring β-carbonyl radical, which adds to vinyl azide to form an iminyl radical with elimination of dinitrogen. Iminyl radical then cyclizes with a...

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Main Author:	Toh, Kah Kah.
Other Authors:	Chiba Shunsuke
Format:	Final Year Project
Language:	English
Published:	2010
Subjects:	DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Online Access:	http://hdl.handle.net/10356/38933
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Institution:	Nanyang Technological University
Language:	English

id	sg-ntu-dr.10356-38933
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spelling	sg-ntu-dr.10356-389332023-02-28T23:19:07Z Catalytic synthesis of azeheterocycles from organic azides. Toh, Kah Kah. Chiba Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis One electron oxidation of bicyclic cyclopropanol, bicyclo[4.1.0]heptan-1-ol by a catalytic amount of Mn(III) promotes ring-expansion to afford 7-membered-ring β-carbonyl radical, which adds to vinyl azide to form an iminyl radical with elimination of dinitrogen. Iminyl radical then cyclizes with an intramolecular carbonyl moiety to give an iminyl radical addition product, 8-phenyl-7-azabicyclo[4.3.1]dec-7-en-6-ol. Upon one-pot treatment with sodium cyanoborohydride, C-O bond reduction occurs first giving 8-phenyl-7-azabicyclo[4.3.1]dec-7-ene, followed by C=N bond reduction giving 8-phenyl-7-azabicyclo[4.3.1]decane in high yield and diasteroselectivity. Bachelor of Science in Chemistry and Biological Chemistry 2010-05-21T01:45:23Z 2010-05-21T01:45:23Z 2010 2010 Final Year Project (FYP) http://hdl.handle.net/10356/38933 en 43 p. application/pdf
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
spellingShingle	DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Toh, Kah Kah. Catalytic synthesis of azeheterocycles from organic azides.
description	One electron oxidation of bicyclic cyclopropanol, bicyclo[4.1.0]heptan-1-ol by a catalytic amount of Mn(III) promotes ring-expansion to afford 7-membered-ring β-carbonyl radical, which adds to vinyl azide to form an iminyl radical with elimination of dinitrogen. Iminyl radical then cyclizes with an intramolecular carbonyl moiety to give an iminyl radical addition product, 8-phenyl-7-azabicyclo[4.3.1]dec-7-en-6-ol. Upon one-pot treatment with sodium cyanoborohydride, C-O bond reduction occurs first giving 8-phenyl-7-azabicyclo[4.3.1]dec-7-ene, followed by C=N bond reduction giving 8-phenyl-7-azabicyclo[4.3.1]decane in high yield and diasteroselectivity.
author2	Chiba Shunsuke
author_facet	Chiba Shunsuke Toh, Kah Kah.
format	Final Year Project
author	Toh, Kah Kah.
author_sort	Toh, Kah Kah.
title	Catalytic synthesis of azeheterocycles from organic azides.
title_short	Catalytic synthesis of azeheterocycles from organic azides.
title_full	Catalytic synthesis of azeheterocycles from organic azides.
title_fullStr	Catalytic synthesis of azeheterocycles from organic azides.
title_full_unstemmed	Catalytic synthesis of azeheterocycles from organic azides.
title_sort	catalytic synthesis of azeheterocycles from organic azides.
publishDate	2010
url	http://hdl.handle.net/10356/38933
_version_	1759858053151195136

Catalytic synthesis of azeheterocycles from organic azides.

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