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Electron-deficient 1-and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity

Jean-Christophe Monbaliu UGent, Kurt Masschelein UGent and Chris Stevens UGent (2011) CHEMICAL SOCIETY REVIEWS. 40(9). p.4708-4739
abstract
Electron-deficient 1- and 2-azabuta-1,3-dienes are reagents intrinsically able to provide a wide range of cyclic and acyclic N-containing building blocks. Depending on their substitution, they behave as dienes for Diels-Alder reactions, as partners for [4+1], [3+2], [2+2]-cycloadditions, for aziridinations and as electrophiles for 1,2 and 1,4-additions. Nowadays, they are a very versatile family of compounds, despite their usual instability and complex reactivity. Four decades of research in this challenging area are reviewed in this critical review: their synthetic aspects and their reactivity towards a wide range of dienophiles, dipoles and nucleophiles are described as well. The introduction focuses on their electronic properties in order to get a clear picture of their reactivity (190 references).
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (review)
publication status
published
subject
keyword
FLUOROALKYL PYRIDINE-DERIVATIVES, AZADIENE-MEDIATED SYNTHESIS, 3-BUTADIENES, AZA-WITTIG REACTION, TRIFLUOROMETHYL-SUBSTITUTED 2-AZA-1, N-VINYLIC PHOSPHAZENES, DIELS-ALDER REACTIONS, ALPHA-AMINO-ACIDS, 4+2 CYCLOADDITION REACTIONS, SECONDARY E-ALLYLAMINES, ASYMMETRIC CONJUGATE ADDITION
journal title
CHEMICAL SOCIETY REVIEWS
Chem. Soc. Rev.
volume
40
issue
9
pages
4708 - 4739
Web of Science type
Review
Web of Science id
000293858500015
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
28.76 (2011)
JCR rank
2/149 (2011)
JCR quartile
1 (2011)
ISSN
0306-0012
DOI
10.1039/c1cs15070g
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1997148
handle
http://hdl.handle.net/1854/LU-1997148
date created
2012-01-19 15:47:01
date last changed
2012-03-07 15:22:29
@article{1997148,
  abstract     = {Electron-deficient 1- and 2-azabuta-1,3-dienes are reagents intrinsically able to provide a wide range of cyclic and acyclic N-containing building blocks. Depending on their substitution, they behave as dienes for Diels-Alder reactions, as partners for [4+1], [3+2], [2+2]-cycloadditions, for aziridinations and as electrophiles for 1,2 and 1,4-additions. Nowadays, they are a very versatile family of compounds, despite their usual instability and complex reactivity. Four decades of research in this challenging area are reviewed in this critical review: their synthetic aspects and their reactivity towards a wide range of dienophiles, dipoles and nucleophiles are described as well. The introduction focuses on their electronic properties in order to get a clear picture of their reactivity (190 references).},
  author       = {Monbaliu, Jean-Christophe and Masschelein, Kurt and Stevens, Chris},
  issn         = {0306-0012},
  journal      = {CHEMICAL SOCIETY REVIEWS},
  keyword      = {FLUOROALKYL PYRIDINE-DERIVATIVES,AZADIENE-MEDIATED SYNTHESIS,3-BUTADIENES,AZA-WITTIG REACTION,TRIFLUOROMETHYL-SUBSTITUTED 2-AZA-1,N-VINYLIC PHOSPHAZENES,DIELS-ALDER REACTIONS,ALPHA-AMINO-ACIDS,4+2 CYCLOADDITION REACTIONS,SECONDARY E-ALLYLAMINES,ASYMMETRIC CONJUGATE ADDITION},
  language     = {eng},
  number       = {9},
  pages        = {4708--4739},
  title        = {Electron-deficient 1-and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity},
  url          = {http://dx.doi.org/10.1039/c1cs15070g},
  volume       = {40},
  year         = {2011},
}

Chicago
Monbaliu, Jean-Christophe, Kurt Masschelein, and Chris Stevens. 2011. “Electron-deficient 1-and 2-azabuta-1,3-dienes: a Comprehensive Survey of Their Synthesis and Reactivity.” Chemical Society Reviews 40 (9): 4708–4739.
APA
Monbaliu, J.-C., Masschelein, K., & Stevens, C. (2011). Electron-deficient 1-and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity. CHEMICAL SOCIETY REVIEWS, 40(9), 4708–4739.
Vancouver
1.
Monbaliu J-C, Masschelein K, Stevens C. Electron-deficient 1-and 2-azabuta-1,3-dienes: a comprehensive survey of their synthesis and reactivity. CHEMICAL SOCIETY REVIEWS. 2011;40(9):4708–39.
MLA
Monbaliu, Jean-Christophe, Kurt Masschelein, and Chris Stevens. “Electron-deficient 1-and 2-azabuta-1,3-dienes: a Comprehensive Survey of Their Synthesis and Reactivity.” CHEMICAL SOCIETY REVIEWS 40.9 (2011): 4708–4739. Print.