Stereospecific photochemical ring expansion of lithiated benzamides

Jonathan Clayden*, Faye E. Knowles, Christel J. Menet

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

26 Citations (Scopus)

Abstract

Treatment of N-benzyl benzamides with a strong base (LDA or t-BuLi) followed by irradiation with a 500 W tungsten lamp provides, according to the substitution pattern of the starting amides, either norcaradienes or cycloheptadienones by overall insertion of the N-benzyl group into the benzamide's aromatic ring system. Chiral benzamides undergo the ring expansion with high (sometimes complete) stereospecificity. The reaction appears to occur via a series of pericyclic reactions (photochemical or thermal sigmatropic rearrangements and thermal electrocyclic reactions) following an initial dearomatizing cyclization.

Original languageEnglish
Pages (from-to)9278-9279
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number31
Early online date11 Jul 2003
DOIs
Publication statusPublished - 6 Aug 2003

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