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