Premium
Water and the Huisgen Cycloaddition Reaction: A Focus on Polar Contributions to the Transition State in the Reactions of Dicyano(phthalazinium)methanide with Substituted Styrenes and Benzylidene Acetones
Author(s) -
Butler Richard N.,
Coyne Anthony G.,
Cunningham William J.,
Moloney Eamon M.,
Burke Luke A.
Publication year - 2005
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200590128
Subject(s) - chemistry , cycloaddition , phthalazine , aryl , polar , medicinal chemistry , kinetic energy , transition state , computational chemistry , stereochemistry , organic chemistry , catalysis , alkyl , physics , quantum mechanics , astronomy
Abstract Synthetic and kinetic studies on the 1,3‐dipolar cycloaddition reactions of dicyano(phthalazin‐2‐ium‐2‐yl)methanide ( 1 ) with some substituted styrenes and ‘benzylidene acetones’ in MeCN and H 2 O containing 10 mol‐% of MeCN are reported. The kinetic data were supported by theoretical calculations. The major products from styrenes were exo ‐2‐aryl‐1,2,3,10b‐tetrahydropyrrolo[2,1‐ a ]phthalazine‐3,3‐dicarbonitriles 3 , and, from ‘benzylidene acetones’, 1‐ endo ,2‐ exo ‐2‐acetyl‐1‐aryl‐1,2,3,10b‐tetrahydropyrrolo[2,1‐ a ]phthalazine‐3,3‐dicarbonitriles 7 . There was no indication that the cycloadditon transition states were more polar in the aqueous environment than in MeCN.