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Synthesis 2022; 54(04): 999-1042
DOI: 10.1055/a-1654-2318
DOI: 10.1055/a-1654-2318
special topic
Cycloadditions – Established and Novel Trends – in Celebration of the 70th Anniversary of the Nobel Prize Awarded to Otto Diels and Kurt Alder
Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions
L.M.S. acknowledges the Council on grants of the President of the Russian Federation (МК-2615.2021.1.3). V.V.V., R.K.S., and V.P.A. acknowledge Saint Petersburg State University (Pure ID: 72776812) for financial support.
Abstract
Acetylene and ethylene are the smallest molecules that contain an unsaturated carbon–carbon bond and can be efficiently utilized in a large variety of cycloaddition reactions. In this review, we summarize the application of these C2 molecular units in cycloaddition chemistry and highlight their amazing synthetic opportunities.
1 Introduction
2 Fundamental Features and Differences of Cycloaddition Reactions Involving Acetylene and Ethylene
3 (2+1) Cycloaddition
4 [2+2] Cycloaddition
5 (3+2) Cycloaddition
6 [4+2] Cycloaddition
7 (2+2+1) Cycloaddition
8 [2+2+2] Cycloaddition
9 The Use of Acetylene and Ethylene Cycloaddition for Deuterium and 13C Labeling
10 Conclusions
Key words
acetylene - cyclizations - cycloaddition reaction - ethylene - heterocyclic compounds - organic synthesisPublication History
Received: 03 September 2021
Accepted after revision: 27 September 2021
Accepted Manuscript online:
27 September 2021
Article published online:
22 December 2021
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Few selected reviews:
Few representative examples: