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 |
|---|---|
| Pages (from-to) | 3732-3738 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 50 |
| Issue number | 20 |
| State | Published - Dec 1 1985 |
| Externally published | Yes |
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Cite this
Regioselectivity in α-cleavage reactions : Arylalkylcyclopropenethiones. / Singh, Sharat; Ramamurthy, Vaidhyanathan.
In: Journal of Organic Chemistry, Vol. 50, No. 20, 01.12.1985, p. 3732-3738.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Regioselectivity in α-cleavage reactions
T2 - Arylalkylcyclopropenethiones
AU - Singh, Sharat
AU - Ramamurthy, Vaidhyanathan
PY - 1985/12/1
Y1 - 1985/12/1
N2 - 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.
AB - 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.
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UR - http://www.scopus.com/inward/citedby.url?scp=33748167851&partnerID=8YFLogxK
M3 - Article
VL - 50
SP - 3732
EP - 3738
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -