51953-08-3Relevant academic research and scientific papers
β-Fisson of 9-Decalinoxyl Radicals: Reversible Formation of 6-Ketocyclodecyl Radical
Beckwith, Athelstan L.J.,Kazlauskas, Rymantas,Syner-Lyons, Mark R.
, p. 4718 - 4722 (2007/10/02)
Rearrangement at 0 deg C of trans-9-decalinyl hypobromide (1trans, X=Br), formed by interaction of 1trans (X=H) with bromine and silver acetate or mercuric oxide, gives 6-bromocyclodecanone(4, X=Br) whereas the same reaction at 81 deg C gives 2-(4-bromobutyl)cyclohexanone (6, X=Br).The cis isomer (1cis, X=Br) behaves similarly.The relative yields of the nitroso dimers, 11, 12, and 13, formed by photolysis of 1cis (X=NO) and 1trans (X=NO), also depend on the reaction temperature.Reduction of 6-bromocyclodecanone (4, X=Br) with tribytylstannane in high concentration gives mainly cis- and trans-9-decalinol, with the former predominating.These results indicate (i) that 9,10-bond fisson of the 9-decalinoxyl radicals, 2cis and 2trans, is rapid but reversible, (ii) that 1,9-bond fisson of 2cis and 2trans is relatively slow and is essentially irreversible under the conditions used here, and (iii) that ring closure of the radical (5) favors formation of the cis product (2cis).
