Substituent Effects on the Iodine-Catalyzed Thermal Cyclization of 3,4-Diphenylbuta-1,3-dienyl Isocyanates: Mechanistic Studies

The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents...

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Veröffentlicht in:	Journal of organic chemistry 2011-12, Vol.76 (23), p.9678-9686
Hauptverfasser:	Chuang, Ta-Hsien, Chang, Wei-Yu, Li, Chien-Fu, Wen, Yu-Chia, Tsai, Chia-Chen
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Catalysis Catalysts: preparations and properties Chemistry Condensed benzenic and aromatic compounds Cyclization Exact sciences and technology General and physical chemistry Iodine - chemistry Isocyanates - chemical synthesis Isocyanates - chemistry Kinetics and mechanisms Molecular Structure Organic chemistry Preparations and properties Reactivity and mechanisms Temperature Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Zusammenfassung:	The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents on the phenyl rings was found to be crucial to the distribution of cyclized products 2–4. The mechanism of the reaction is also discussed.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo2017247