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:
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
InChI=1/O2S/c1-3-2
InChI=1/C4H6O2S/c5-7(6)3-1-2-4-7/h1-2H,3-4H2
KAKZBPTYRLMSJV-UHFFFAOYAZ
RAHZWNYVWXNFOC-UHFFFAOYAT
MBDNRNMVTZADMQ-UHFFFAOYAO
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.
https://doi.org/10.1351/goldbook.
