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electrocyclic reaction

Also contains definitions of: conrotatory, disrotatory

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:
E01948-1
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.
E01948-2
or 'disrotatory' (or suprafacial ) if one terminus rotates in a clockwise and the other in a counter-clockwise sense, e.g.
E01948-3
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-
UBFBTMRIJJRZOA-WAYWQWQTBE
InChI=1/C8H12/c1-7-5-3-4-6-8(7)2/h3-8H,1-2H3
CJSMAFKHKCZRCX-UHFFFAOYAZ
InChI=1/C10H16/c1-9(2)7-5-6-8-10(3)4/h5-8H,1-4H3/b6-5-
UBFBTMRIJJRZOA-WAYWQWQTBE
InChI=1/C8H12/c1-7-5-3-4-6-8(7)2/h3-8H,1-2H3
CJSMAFKHKCZRCX-UHFFFAOYAZ
InChI=1/C6H8/c1-3-5-6-4-2/h3-6H,1-2H2/b6-5-
AFVDZBIIBXWASR-WAYWQWQTBR
InChI=1/C6H8/c1-2-4-6-5-3-1/h1-4H,5-6H2
MGNZXYYWBUKAII-UHFFFAOYAH
InChI=1/C5H4/c1-3-5-4-2/h1-2H2
UNSWNZFTRPSXHQ-UHFFFAOYAI
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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.E01948.
Original PDF version: http://www.iupac.org/goldbook/E01948.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 The PDF version is out of date and is provided for reference purposes only.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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