A
molecular rearrangement that involves the formation of a σ-bond between the termini of a fully
conjugated linear π-electron system (or a linear fragment of a π-electron system) and a decrease
by one in the number of π-bonds, or the reverse of that process. For example:
The stereochemistry of such a process is termed '
conrotatory' or
antarafacial if the substituents at the interacting termini of the conjugated system both rotate
in the same sense, e.g.
or '
disrotatory' (or
suprafacial ) if one terminus rotates in a clockwise and the other in a counter-clockwise sense,
e.g.
Source:
PAC, 1994, 66, 1077
(Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994))
on page 1108
InChI=1/C10H16/c1-9(2)7-5-6-8-10(3)4/h5-8H,1-4H3/b6-5-
InChI=1/C8H12/c1-7-5-3-4-6-8(7)2/h3-8H,1-2H3
InChI=1/C10H16/c1-9(2)7-5-6-8-10(3)4/h5-8H,1-4H3/b6-5-
InChI=1/C8H12/c1-7-5-3-4-6-8(7)2/h3-8H,1-2H3
InChI=1/C6H8/c1-3-5-6-4-2/h3-6H,1-2H2/b6-5-
InChI=1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
InChI=1/C5H4/c1-3-5-4-2/h1-2H2
UBFBTMRIJJRZOA-WAYWQWQTBE
CJSMAFKHKCZRCX-UHFFFAOYAZ
UBFBTMRIJJRZOA-WAYWQWQTBE
CJSMAFKHKCZRCX-UHFFFAOYAZ
AFVDZBIIBXWASR-WAYWQWQTBR
MGNZXYYWBUKAII-UHFFFAOYAH
UNSWNZFTRPSXHQ-UHFFFAOYAI
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.
