Anti-markovnikov addition of nucleophiles to a non-conjugated olefin via single electron transfer photochemistry
✍ Scribed by Paul G. Gassman; Kyle J. Bottorff
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 256 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
Nucleophilic solvent has been added regiospecifically in an anti-Markovnikov manner to a simple non-conjugated olefin, l-methylcyclohexene, through single electron transfer induced photochemistry using the 1-cyanonaphthalene -biphenyl pair for achieving photooxidation.
Although photoinduced additions of nucleophiles to derivatives of styrene and stilbene are well known, ' relatively little is known about the photoinduced addition of nucleophiles to simple nonconjugated olefins. Kropp has described the addition of ethanol to 2,3-dimethyl-2-butene via direct irradiation and suggested the presence of an excited Rydberg state.2 Lewis and DeVoe examined the photosensitized addition of methanol to this same olefin, albeit in low yield.3-5