TY  - UNPB
ID  - pittir7705
UR  - http://d-scholarship-dev.library.pitt.edu/7705/
A1  - Turner, Tiffany Renee
TI  - Concentration Studies on the Radical Cyclizations of Enol acetates and Enol carbonates and the Possible Formation of 4-Hydrindanones via an Uncommon Acyl Radical Fragmentation
Y1  - 2006/06/29/
N2  - Recently, Uta Wille and coworkers proposed a novel non-chain, self-terminating, oxidative radical cyclization that ends with the uncommon homolytic cleavage of an acyl-oxygen bond to give a ketone and an acyl radical (J. Amer. Chem. Soc. 2002, 124 (1), 14-15). We present the results of our study into this type of unusual radical fragmentation. Our focus was on initiating radical intermediates 53a,b thru thermal means using Bu3SnH to produce ketone 54 as opposed to photo-induced methods used by Wille. In our work, we were unable to produce 54 in sufficient yields, but we were able to isolate carbonyl compounds 62-63?,?. Based on these results, we cannot rule out an alternative polar fragmentation.
AV  - public
KW  - acyl radical fragmentation; hydrindanones; radical cyclization
ER  -