Photochemistry of δ-hydroxybutyl α,β-unsaturated γ,δ-epoxy nitriles. Formation of spiro ketals

Autor:	Takao Nakano, Masanori Sakamoto, Ikuo Iida, Keitaro Ishii, Tatsuya Zenko, Takehiko Nishio, Masashi Kotera
Rok vydání:	1995
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Double bond Chemistry Ylide Organic Chemistry Solvent polarity Ether General Chemistry Crystal structure Physical and Theoretical Chemistry Medicinal chemistry
Zdroj:	Liebigs Annalen. 1995:19-27
ISSN:	1099-0690 0947-3440
DOI:	10.1002/jlac.199519950106
Popis:	Photocyclization reactions of δ-hydroxybutyl α,β-unsaturated γ,δ-epoxy nitriles 4a, b at 254 nm lead to spiro ketals 5a, b and 6a, b arising from the carbonyl ylide intermediate A. The spiro ketal 6b containing an endocyclic double bond is transformed to spiro ether 16 by an acid-catalyzed 1,3-sigmatropic rearrangement. The ratio of spiro ketals 5 and 6 has been shown to depend on solvent polarity and acidity of additives. Application to the synthesis of pheromones is presented. X-ray crystal structure analyses are performed on dispiro compound 18 and spiro ester 25.
Databáze:	OpenAIRE
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