Steric Requirements in the Cyclization of Naphthalene Derivatives

Carl Djerassi, George R. Pettit

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

While polyphosphoric acid cyclization followed by dehydrogenation of γ-(2-naphthyl)butyraldehyde (Ia) yields exclusively phenanthrene, the corresponding substituted ketones Ib, Ic and Id lead predominantly to linear cyclization products of the anthracene series. These results are ascribed to steric interference of the 4 and 5 substituents in the phenanthrene series and are not operative in the next lower homolog as demonstrated by the cyclization of 5-(2′-naphthyl)pentan-3-one (VIc) to 1-ethyl-3H-benz [e]indene (VII).

Original languageEnglish (US)
Pages (from-to)393-396
Number of pages4
JournalJournal of Organic Chemistry
Volume22
Issue number4
DOIs
StatePublished - Jan 1 1957
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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