Acceleration of the 4-exo radical cyclization to a synthetically useful rate. Cyclization of the 2,2-dimethyl-5-cyano-4-pentenyl radical
作者： Seung-Un Park , Thomas R. Varick , Martin Newcomb
DOI: 10.1016/S0040-4039(00)89002-4
关键词:
摘要: The title radical, formed in the reaction of corresponding bromide with Bu3SnH, cyclizes a 4-exo fashion to give (3,3-dimethylcyclobutyl)cyanomethyl radical. At 50 °C, rate constant for cyclizafion is 1.9 x 104 s−1.
elsevier.com
sci-hub.se 参考文章(24)
Tullio Caronna, Attilio Citterio, Maurizio Ghirardini, Francesco Minisci, Nucleophilic character of alkyl radicals—XIII Tetrahedron. ,vol. 33, pp. 793- 796 ,(1977) , 10.1016/0040-4020(77)80194-4
Paul Dowd, Soo Chang Choi, A new tributyltin hydride-based rearrangement of bromomethyl .beta.-keto esters. A synthetically useful ring expansion to .gamma.-keto esters Journal of the American Chemical Society. ,vol. 109, pp. 3493- 3494 ,(1987) , 10.1021/JA00245A069
Martin Newcomb, Jere Kaplan, Rate constants for the analysis of alkyl iodide mechanistic probe studies Tetrahedron Letters. ,vol. 29, pp. 3449- 3450 ,(1988) , 10.1016/0040-4039(88)85186-4
Nicholas J.G Cox, Gerald Pattenden, Stuart D Mills, Radical macrocyclisations in synthesis. A new approach to mukulol and marine cembranolide lactones Tetrahedron Letters. ,vol. 30, pp. 621- 624 ,(1989) , 10.1016/S0040-4039(00)95271-7
Gary E. Keck, Eric J. Enholm, John B. Yates, Michael R. Wiley, One electron C-C bond forming reactions via allylstannanes: scope and limitations Tetrahedron. ,vol. 41, pp. 4079- 4094 ,(1985) , 10.1016/S0040-4020(01)97185-6
Martin Newcomb, Anne G. Glenn, William G. Williams, Rate constants and Arrhenius functions for rearrangements of the 2,2-dimethyl-3-butenyl and (2,2-dimethylcyclopropyl)methyl radicals Journal of Organic Chemistry. ,vol. 54, pp. 2675- 2681 ,(1989) , 10.1021/JO00272A042
Martin. Newcomb, Seung Un. Park, N-Hydroxypyridine-2-thione esters as radical precursors in kinetic studies. Measurements of rate constants for hydrogen-atom-abstraction reactions Journal of the American Chemical Society. ,vol. 108, pp. 4132- 4134 ,(1986) , 10.1021/JA00274A046
Seung Un. Park, Sung Kee. Chung, Martin. Newcomb, Acceptor, donor, and captodative stabilization in transition states of 5-hexen-1-yl radical cyclizations Journal of the American Chemical Society. ,vol. 108, pp. 240- 244 ,(1986) , 10.1021/JA00262A009
Gilbert. Stork, Philip Michael. Sher, A catalytic tin system for trapping of radicals from cyclization reactions. Regio- and stereocontrolled formation of two adjacent chiral centers Journal of the American Chemical Society. ,vol. 108, pp. 303- 304 ,(1986) , 10.1021/JA00262A024
Derek H.R. Barton, David Crich, William B. Motherwell, The invention of new radical chain reactions. Part VIII. Radical chemistry of thiohydroxamic esters; A new method for the generation of carbon radicals from carboxylic acids Tetrahedron. ,vol. 41, pp. 3901- 3924 ,(1985) , 10.1016/S0040-4020(01)97173-X