Photolysis of cis- and trans-2-(3,5-dimethoxyphenyl)cyclopentyl methanesulfonate. Stereoelectronic requirement for photosolvolysis
✍ Scribed by David A. Jaeger; Emily A. Bernhardt
- Book ID
- 104219921
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- French
- Weight
- 260 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
On irradiation in methanol, trans-2-(3,5_dimethoxyphenyl)cyclopentyl methanesulfonate underwent photosolvolysis whereas the cis-isomer did not; thus, for photosolvolysis there exists atrans-requirement of excited aryl group and leaving group.
There have been several reports of photosolvolysis of 2-arylalkyl and related systems. 1
In particular, we reported la that of la in aqueous methanol, -which yielded 2 and 2 as the major products.
With deuterated analogue 2, these products were produced with 100% scrambling of the labeled carbon between the l-and 2-positions of the ethyl group. A mechanism involving phenonium ion intermediate 4 was proposed based on these and other results.