Abstract
Photoreactions of several arylalkylcyclopropenethiones (1b-e) have been investigated. The products formed have been rationalized on the basis of α-cleavage as the primary photoprocess. The photochemical α-cleavage is presumed to originate from the lowest excited nπ* triplet state. A regioselective α-cleavage reaction has been observed and this unusual regioselectivity is explained on the basis of close approach of the ground-state energy surface of the diradical/carbene, the primary intermediates, to the excited triplet-state surface of cyclopropenethiones. Reactions originating from both triplet and singlet thioketene carbene have been observed upon photolysis of arylalkylcyclopropenethiones.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3732-3738 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 50 |
| Issue number | 20 |
| DOIs | |
| State | Published - Oct 1985 |
| Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Singh, S., & Ramamurthy, V. (1985). Regioselectivity in α-Cleavage Reactions: Arylalkylcyclopropenethiones. Journal of Organic Chemistry, 50(20), 3732-3738. https://doi.org/10.1021/jo00220a012