The chemistry of cyclobutenediones has been extensively investigated' by many workers, but in contrary very little are known of their behavior as dipolarophiles and on this respect is mentioned the reaction of diazomethane with diphenylcyclobutenedione studied by Ried et a13. On
Stereoselectivities of mesitonitrile oxide cycloadditions to 7-substituted norbornadienes
โ Scribed by Lorenzo Dal Bola; Marco De Amici; Carlo De Micheli; Remo Gandolfi; K.N. Houk
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 249 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
The stereochemistries of cycloadditions of mesitonitrile oxide to norbomadiene and nine 7-substituted derivatives have been investigated.
The stereoselectivities are controlled primarily by torsional effects which are altered by 7-substituents.
๐ SIMILAR VOLUMES
The structures of 7-substituted norbomadienes have been studied theoretically with the 3-21G basis set. The stereoselectivities and rates of electrophilic cycloadditions of HCCP to these norbomadienes am rational&d.
Benzonitrile oxide cycloadds preferentially anti to the substituents of cis-3,5-di-X-cyclopentenes, where X = OMe, OAc, CCCPh, Br, Cl, and OH. Higher stereoselectivities are found for cis-2,5-di-X-2,5\_dihydrofurans. The origins of these selectivities, and contrasts with azlic and cyclobutene analog