@article { ISI:000308628900033, title = {New synthetic route for 1,2-diketo compounds using unexpected C-C bond cleavage by PCC}, journal = {Tetrahedron Letters}, volume = {53}, number = {39}, year = {2012}, month = {SEP}, pages = {5327-5330}, publisher = {PERGAMON-ELSEVIER SCIENCE LTD}, address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}, abstract = {

An efficient method has been established for the preparation of 1,2-diketones by unexpected C-C bond cleavage in 4-keto-2-hydroxy esters using pyridiniumchlorochromate (PCC). (c) 2012 Elsevier Ltd. All rights reserved.

}, keywords = {1, 2-Diketones, C-C bond cleavage, PCC}, issn = {0040-4039}, doi = {10.1016/j.tetlet.2012.07.095}, author = {Bhosale, Shrikar M. and Momin, Aadil A. and Gawade, Rupesh L. and Puranik, Vedavati G. and Kusurkar, Radhika S.} } @article { ISI:000377612300015, title = {Scandium triflate catalyzed unexpected cleavage of C-C bonds in ynones}, journal = {Arkivoc}, number = {2}, year = {2016}, month = {NOV}, pages = {223-232}, publisher = {ARKAT USA INC}, address = {C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA}, abstract = {

An unexpected C-C bond cleavage in ynones in the presence of catalytic amounts of Sc(OTf)(3) in methanol under microwave irradiation has been discussed. The effect of substituent on the regioselectivity of C-C bond cleavage has carefully been addressed by employing various ynones derivatives. The mechanism has been proposed for the observed regioselectivity.

}, keywords = {C-C bond cleavage, Esters, Ketones, scandium triflate, ynones}, issn = {1551-7004}, doi = {10.3998/ark.5550190.p009.244}, author = {Kavthe, Rahul D. and Bansode, Avinash H. and Patil, Nitin T.} } @article {50099, title = {Electrochemical generation of N-centered radicals and their reactivity toward cyclization and subsequent C--C bond cleavage}, journal = {Helvetica Chimica Acta}, volume = {109}, year = {2026}, month = {APR}, type = {Article}, abstract = {

N-containing heterocycles are widely used in medicinal chemistry, and they can be synthesized efficiently by the intramolecular cyclization of N-centered radicals. Furthermore, N-centered radicals also act as excellent hydrogen atom transfer (HAT) reagents. On the other hand, nitrogen atoms in the nitrogen-containing heterocycles are used as a handle to cleave stable five and six-membered rings. However, the electrochemical generation of N-centered radicals and their application in forming heterocycles have been extensively studied. Study beyond cyclization remains largely unexplored; in this manuscript, we summarize our new findings as follows. Under electrochemical conditions, the N \& horbar;H bond is cleaved, forming an N-centered radical that adds to the double bond in a 6-endo-trig cyclization fashion. The newly formed C-centered radical reacts with oxygen and undergoes C \& horbar;C bond cleavage to form the corresponding carbonyl compounds. The reactivity is dependent on the substituents present on nitrogen. In the case of aromatic amine-derived amide, the TEMPO trapping cyclization product was isolated. A mechanism has been proposed to explain the formation of the products.

}, keywords = {C-C bond cleavage, cyclization, N-centered radical, N-heterocycles, oxidative ring opening}, issn = {0018-019X}, doi = {10.1002/hlca.202500225}, author = {Suryawanshi, Sharad M. and Singh, Mayuri and Samanta, Ramesh C.} }