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
✍ Scribed by Richard N. Butler; Anthony G. Coyne; William J. Cunningham; Eamon M. Moloney; Luke A. Burke
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- German
- Weight
- 377 KB
- Volume
- 88
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
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.