Photochemistry of vinyl halides. Formation of benzofurans by photolysis of. beta. -(o-methoxyphenyl)vinyl bromides
Photolysis of ..beta..,..beta..-bix(o-methoxyphenyl)-substituted vinyl bromides gave benzofuran derivatives which are derived from an intramolecular nucleophilic attack of the methoxyl group on an intermediate vinyl cation. With ..cap alpha..-aryl-substituted vinyl bromides, only one type of benzofuran derivative was detected. However, when the ..cap alpha.. substituent was a hydrogen or a methyl group, two isomeric benzofurans were formed, one via the unrearranged vinyl cation and the other via an (o-methoxyphenyl)-rearranged vinyl cation. Irradiation of ..cap alpha..-methyl-..beta..,..beta..-bis-(o-methoxyphenyl)vinyl bromide in nucleophilic solvent, i.e., methanol, did not result in solvent-incorporated products. In the photolysis of ..beta..-(o-methoxyphenyl)-substituted vinyl bromides a selectivity-reactivity relationship between the cyclization and the rearrangement of the initially formed vinyl cation was observed.
- Research Organization:
- Kyushu Univ., Fukuoka, Japan
- OSTI ID:
- 5313902
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 46:26; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400500* -- Photochemistry
AROMATICS
BASES
BENZOFURANS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CONCENTRATION RATIO
DATA
DECOMPOSITION
DERIVATIZATION
EXPERIMENTAL DATA
FURANS
HETEROCYCLIC COMPOUNDS
INFORMATION
LEWIS BASES
NUMERICAL DATA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMICAL REACTIONS
PHOTOLYSIS
REACTION INTERMEDIATES
STABILITY
YIELDS