Chemistry of 1,3-dioxepins. 111. Dehydrohalogenation of 5,6-dihalogen-1,3-dioxepanes with strong bases

Scientific paper - Original scientific paper

• Author: Mladen V. Proštenik
• Author: Miljenko Dumić
• Author: Ivan Butula; MBZ: 6372
• Author's institution: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of medicinal chemistry)
• Scientific / art field, discipline and subdiscipline: BIOMEDICINE AND HEALTHCARE; Pharmacy; Pharmacy

Abstract (english)

Dehydrohalogenation of 5,6-dihalogen-1,3-dioxepanes II with
KOH/MeOH or NaOCH3/MeOH under controlled reaction conditions
gave mainly 5-halogen-4,7-dihydro-1,3-dioxepines III. Further substitution
of vinylic-bromine in III whit KO-t-Bu/tert-BuOH or
KOH/MeOH led to corresponding 5-substituted-4,7-dihydro-1,3-
-dioxepines some of which underwent spontaneous isomerization
to 6,7-dihydro-1,3-dioxepines. Substitution of vinylic-bromine
appeared to follow an elimination-addition mechanism with initial
formation of an intermediate with a triple bond.

• Language: english
• Publication type: Scientific paper - Original scientific paper
• Publication status: Published
• Peer review: Peer review - international
• Publication version: Published version
• Journal title: Croatica Chemica Acta
• Numbering: vol. 57, no. 2, pp. 281-288
• p-ISSN: 0011-1643
• e-ISSN: 1334-417X
• URN:NBN: urn:nbn:hr:163:415423
• Publication: 1984
• Document URL: https://hrcak.srce.hr/194164
• Type of resource: Text
• Access conditions: Open access
• Created on: 2020-04-30 14:46:30