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.
Thermal rearrangements of 7-substituted norbornadienes to cycloheptatrienes
โ Scribed by R.K. Lustgarten; Herman G. Richey Jr.
- Publisher
- Elsevier Science
- Year
- 1966
- Tongue
- French
- Weight
- 145 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
The isomerization of norbornadiene to cycloheptatriene takes place under relatively severe thermal conditions (425");3 however 7-alkoxy or 7-phenyl substituted norbornadienes undergo a more facile (170") thermal rearrangement to the corresponding tropyl derivative. 4 A similar reaction involving con
Nechanistic aspects of thermal sigmatropic rearrangements in cycloheptatrienes have been studied extensively.2 In contrast, the synthetic potential of these isomerization reactions has been exploited only recently. For example, a facile entry to tricyclo[4.3.1.03g8]decane (protoadamantane) derivativ
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.