Vinylcyclopropylacyl and polyeneacyl radicals. Intramolecular ketene alkyl radical additions in ring synthesis
作者:Beno�t De Boeck、Nicola M. A. Herbert、Nicole M. Harrington-Frost、Gerald Pattenden
DOI:10.1039/b413816n
日期:——
intramolecular cyclisations of their ketene alkyl radical intermediates. Under the same radical-initiating conditions the selenyl esters derived from o-vinylbenzoic acid and o-vinylcinnamic acid undergo intramolecular cyclisations producing 1-indanone and 5,6-dihydrobenzocyclohepten-7-one respectively in 60-70% yields. A tandem radical cyclisation from the alpha,beta,gamma,delta-diene selenyl ester 31 provides
在回流的苯中用Bu(3)SnH-AIBN处理多种取代的乙烯基环丙基硒基酯,例如11,会导致相应的酰基自由基中间体,这些中间体会通过其乙烯酮烷基自由基等价物进行重排和分子内环化,从而在50-60中生成环己烯酮% 屈服。相比之下,用Bu(3)SnH-AIBN处理共轭三烯硒烯基酯,例如32,可通过其烯酮烷基自由基中间体的分子内环化反应生成取代的2-环戊烯酮。在相同的自由基引发条件下,衍生自邻乙烯基苯甲酸和邻乙烯基肉桂酸的硒基酯进行分子内环化,分别以60-70%的产率产生1-茚满酮和5,6-二氢苯并环庚基-7-one。从alpha,beta,gamma串联串联进行的环化反应