Synthesis of highly condensed heterocycles using radical reactions

Ganguly, Ashit K.; Wang, C.H.; Misiaszek, J.; Chan, T.M.; Pramanik, Birendra N.; McPhail, Andrew T.

doi:10.1016/j.tetlet.2004.09.181

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Neophyl Rearrangement1

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Cited by 6 publications

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“…In one example a spirointermediate has been trapped in low yield by 5-exo cyclisation onto a pendant alkene. 146…”

Section: Neophyl Rearrangementmentioning

confidence: 99%

Synthesis using aromatic homolytic substitution—recent advances

2007

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This critical review aims at presenting recent developments in intramolecular aromatic homolytic substitution which has become one of the common methodologies in modern synthesis. The application of Bu3SnH-mediated cyclisations have proved especially useful. The critical review illustrates the mechanistic considerations required for planning synthetic applications and a wide range of synthetic protocols and natural product syntheses are shown. The latest evidence for the mechanisms involved in aromatic homolytic substitution are presented. (152 references).

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“…In one example a spirointermediate has been trapped in low yield by 5-exo cyclisation onto a pendant alkene. 146…”

Section: Neophyl Rearrangementmentioning

confidence: 99%

Synthesis using aromatic homolytic substitution—recent advances

2007

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show abstract

“…Previous studies seem to demonstrate that simplistic ideas related to a kinetically driven pathway and a preference for the formation of six- over seven-membered rings are invalid. , Thus, to explain the regiochemistry of ring closure, we turned to quantum mechanical calculations. Prior work in this area has been communicated by Ganguly and co-workers …”

mentioning

confidence: 99%

“…Bearing in mind previous reports from Motherwell and Ganguly, and our own previous results, the radical reaction was attempted in the presence of TTMSS and azobis(cyclohexanenitrile) (ABCN) under thermal conditions.…”

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confidence: 99%