Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.

β-keto acids and vinyl azides are found to be promising precursors for the synthesis of pyrroles with Mn(acac)3 as a catalyst. One electron oxidation of β-keto acids by Mn(acac)3 induces decarboxylation to afford α-keto radicals, which then add on to vinyl azides, leading to the formation of iminyl...

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Main Author:	Ng, Eileen Pei Jian.
Other Authors:	Chiba Shunsuke
Format:	Final Year Project
Language:	English
Published:	2010
Subjects:	DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds
Online Access:	http://hdl.handle.net/10356/40466
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Institution:	Nanyang Technological University
Language:	English

id	sg-ntu-dr.10356-40466
record_format	dspace
spelling	sg-ntu-dr.10356-404662023-02-28T23:15:06Z Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids. Ng, Eileen Pei Jian. Chiba Shunsuke School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds β-keto acids and vinyl azides are found to be promising precursors for the synthesis of pyrroles with Mn(acac)3 as a catalyst. One electron oxidation of β-keto acids by Mn(acac)3 induces decarboxylation to afford α-keto radicals, which then add on to vinyl azides, leading to the formation of iminyl radicals with elimination of dinitrogen. Intramolecular cyclization of the iminyl radical with a carbonyl moiety gives pyrrole after dehydration with regeneration of the Mn(III) complex. Bachelor of Science in Chemistry and Biological Chemistry 2010-06-16T01:35:29Z 2010-06-16T01:35:29Z 2010 2010 Final Year Project (FYP) http://hdl.handle.net/10356/40466 en 37 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::Heterocyclic compounds
spellingShingle	DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds Ng, Eileen Pei Jian. Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
description	β-keto acids and vinyl azides are found to be promising precursors for the synthesis of pyrroles with Mn(acac)3 as a catalyst. One electron oxidation of β-keto acids by Mn(acac)3 induces decarboxylation to afford α-keto radicals, which then add on to vinyl azides, leading to the formation of iminyl radicals with elimination of dinitrogen. Intramolecular cyclization of the iminyl radical with a carbonyl moiety gives pyrrole after dehydration with regeneration of the Mn(III) complex.
author2	Chiba Shunsuke
author_facet	Chiba Shunsuke Ng, Eileen Pei Jian.
format	Final Year Project
author	Ng, Eileen Pei Jian.
author_sort	Ng, Eileen Pei Jian.
title	Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
title_short	Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
title_full	Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
title_fullStr	Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
title_full_unstemmed	Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.
title_sort	mn(iii)-catalyzed synthesis of pyrroles from vinyl azides and b-keto acids.
publishDate	2010
url	http://hdl.handle.net/10356/40466
_version_	1759855702094905344

Mn(III)-catalyzed synthesis of pyrroles from vinyl azides and B-keto acids.

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