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Photochemical cycloadditions of 2,3-dihalobenzo(b)thiophenes: stereochemical and mechanistic results

Journal Article · · J. Org. Chem.; (United States)
DOI:https://doi.org/10.1021/jo00158a028· OSTI ID:5840360
 [1]; ; ;
  1. Bowling Green State Univ., OH
+ Show Author Affiliations

Synthetic approaches to 2-thia-3,4-benzobicyclo(3.2.0)-1,3,6-heptatriene and to 2-thia-3,4-benzobicyclo(3.2.0)-1,3-heptadiene required halogenated cyclobutanes derived from (/sub ..pi../2/sub s/ + /sub ..pi../2/sub s/) photocycloadditions of 2,3-dichlorobenzo(b)thiophene and either vinyl bromide or 1,2-dichloroethylene. Addition reactions of vinyl bromide and dichloroethylene with 2,3-dichlorobenzo(b)thiophene and with 2,3-dibromobenzo(b)thiophene are reported. X-ray crystal structures of the two adducts derived from vinyl bromide and 2,3-dibromobenzo(b)thiophene specify their stereochemistry. The adducts to 2,3-dibromobenzo(b)thiophene are linear, and structure determinations for these compounds are also reported. 2 figures, 1 table.

OSTI ID:
5840360
Journal Information:
J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 48:10; ISSN JOCEA
Country of Publication:
United States
Language:
English

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ADDUCTS
AROMATICS
BROMINATED ALIPHATIC HYDROCARBONS
BROMINATED AROMATIC HYDROCARBONS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHLORINATED ALIPHATIC HYDROCARBONS
CHLORINATED AROMATIC HYDROCARBONS
COHERENT SCATTERING
CRYSTAL STRUCTURE
CRYSTALLOGRAPHY
DATA
DIFFRACTION
ENERGY-LEVEL TRANSITIONS
EXCITATION
EXPERIMENTAL DATA
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATED AROMATIC HYDROCARBONS
HETEROCYCLIC COMPOUNDS
INFORMATION
IONIZATION
MOLECULAR STRUCTURE
NMR SPECTRA
NUMERICAL DATA
ORGANIC BROMINE COMPOUNDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PHOTOCHEMICAL REACTIONS
PHOTOIONIZATION
SCATTERING
SPECTRA
STEREOCHEMISTRY
X-RAY DIFFRACTION
YIELDS