In:
European Journal of Organic Chemistry, Wiley, Vol. 2003, No. 15 ( 2003-08), p. 2941-2946
Abstract:
Depending on the substituent and the heteroelements of an unsaturated three‐membered ring system of the methylenecyclopropane/1‐methylcyclopropene type, the double bond may be preferentially exo‐ or endocyclic. This preference may be considered as a combination of substituent and ring‐strain effects. The substituent effect is a composite one, encompassing both exocyclic olefinic strain and tautomeric preference. The preference for exocyclic unsaturation increases in the order =CH 2 〈 =NH 〈 =PH 〈 =O for the considered substituents. The higher the ring‐strain, the higher the propensity for exocyclic unsaturation. The low‐strain 2 H ‐phosphirenes favor endocyclic unsaturation, except for the 3‐OH‐substituted species where the strong C=O double bond is the determining factor. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2003:15
DOI:
10.1002/ejoc.200300120
Language:
English
Publisher:
Wiley
Publication Date:
2003
detail.hit.zdb_id:
1475010-7