Can the high reactivity of azomethine betaines in [3 + 2] cycloaddition reactions be explained using singlet-diradical character descriptors? What molecular mechanism is actually involved in these cycloadditions?-Reference-Cited by-同舟云学术

Can the high reactivity of azomethine betaines in [3 + 2] cycloaddition reactions be explained using singlet-diradical character descriptors? What molecular mechanism is actually involved in these cycloadditions?

Published:2015 Issue:76 Volume:5 Page:62248-62259
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Emamian Saeedreza¹²³⁴⁵,Lu Tian⁶⁷⁸,Moeinpour Farid⁹¹⁰³¹¹⁵

Affiliation:

1. Chemistry Department

2. Shahrood Branch

3. Islamic Azad University

4. Shahrood

5. Iran

6. Beijing Kein Research Center for Natural Sciences

7. Beijing 100022

8. P. R. China

9. Department of Chemistry

10. Bandar Abbas Branch

11. Bandar Abbas

Abstract

The singlet-diradical character of AZBs makes these TACs reactive in [3 + 2] cycloaddition toward ethylene taking place via a non-concerted one-step mechanism.

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2015/RA/C5RA08614K

Reference28 articles.

1. W. Carruthers , Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990

2. Understanding the mechanisms of [3+2] cycloaddition reactions. The pseudoradical versus the zwitterionic mechanism

3. A. Padwa and W. H.Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, John Wiley & Sons, Hoboken, New Jersey, 2002

4. A DFT analysis of the participation of zwitterionic TACs in polar [3+2] cycloaddition reactions

5. A Clear Correlation between the Diradical Character of 1,3-Dipoles and Their Reactivity toward Ethylene or Acetylene

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