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cheletropic reaction

A form of cycloaddition across the terminal atoms of a fully conjugated system with formation of two new σ-bonds to a single atom of the ('monocentric') reagent. There is formal loss of one π-bond in the substrate and an increase in coordination number of the relevant atom of the reagent. An example is the addition of sulfur dioxide to butadiene:
C01014
The reverse of this type of reaction is designated 'cheletropic elimination'.
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1094
InChI=1/C4H6/c1-3-4-2/h3-4H,1-2H2
KAKZBPTYRLMSJV-UHFFFAOYAZ
InChI=1/O2S/c1-3-2
RAHZWNYVWXNFOC-UHFFFAOYAT
InChI=1/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2
MBDNRNMVTZADMQ-UHFFFAOYAO
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Cite as:
IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.C01014.
Original PDF version: http://www.iupac.org/goldbook/C01014.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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