In the lowest excited triplet state, benzil (1) adds highly regio‐ and stereoselectively to the olefin 2‐morpholinoacrylonitrile (2) to form solely the oxetane 5.
Photochemical reactions of carbonyl compounds in solution The Paterno-Büchi reaction
✍ Scribed by N.C. Yang; Manesse Nussim; Margaret J. Jorgenson; Steven Murov
- Publisher
- Elsevier Science
- Year
- 1964
- Tongue
- French
- Weight
- 369 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
In a series of elegant investigations Hammond demonstrated that the triplet state is the reactive state in the photoreductions of aromatic car-bony1 compounds and the photosensitized reactions by these compounds.' Independent contributions by Porters2 F!itts3 and Backstrom are in agreeaaent with this finding. 'Pne importance of the nature of the low-lying triplet state is illustrated by the difference in the behavior of benzophenone and acetonaphthone. The former has an n-.x* low-lying triplet stats and is photoreduced by alcohols and alkylbeneenes; the latter has a n-r%* low-lying triplet state and is only photoreduced in the presence of strong reducing agents.5'6 In this investigation, the photochemical formation of oxetanes (1) G.
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