TY - JOUR
T1 - Bimanes. 10. Photochemical Rearrangement of 1,5-Diazabicyclo[3.3.0]octa-3,7-diene-2,6-diones (9,10-Dioxa-anti-bimanes)
AU - Kanety, Hannah
AU - Dodiuk, Hanna
AU - Kosower, Edward M.
PY - 1982
Y1 - 1982
N2 - 1,5-Diazabicyclo[3.3.0]octa-3,7-diene-2,6-diones (9, 10-dioxa-anti-bimanes) rearrange quantitatively on irradiation in the 320-nm absorption band to isomeric lactones, one from symmetrical bimanes and two from unsymmetrical bimanes (“mixed” bimanes). The quantum yield of lactone is often high and depends upon bimane substitution and solvent viscosity. Fast intersystem crossing (Huppert et al.4), oxygen inhibition of lactone formation, and efficient formation of lactone via a triplet sensitizer implicate the triplet as a key intermediate. The suggested mechanism of lactone formation involves a twisted π-π* triplet.
AB - 1,5-Diazabicyclo[3.3.0]octa-3,7-diene-2,6-diones (9, 10-dioxa-anti-bimanes) rearrange quantitatively on irradiation in the 320-nm absorption band to isomeric lactones, one from symmetrical bimanes and two from unsymmetrical bimanes (“mixed” bimanes). The quantum yield of lactone is often high and depends upon bimane substitution and solvent viscosity. Fast intersystem crossing (Huppert et al.4), oxygen inhibition of lactone formation, and efficient formation of lactone via a triplet sensitizer implicate the triplet as a key intermediate. The suggested mechanism of lactone formation involves a twisted π-π* triplet.
UR - http://www.scopus.com/inward/record.url?scp=33845554477&partnerID=8YFLogxK
U2 - 10.1021/jo00341a006
DO - 10.1021/jo00341a006
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AN - SCOPUS:33845554477
SN - 0022-3263
VL - 47
SP - 207
EP - 213
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -