Structural correction of the 3-methylindole oxidatively-coupled dimer

✍ Scribed by Ke-Qing Ling; Tong Ren; John D. Protasiewicz; Lawrence M. Sayre

• Book ID: 104251933
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 145 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)01623-4

✦ Synopsis

The main product of the horseradish peroxidase-mediated oxidative coupling of 3-methylindole by H 2 O 2 has been found to be the same compound previously obtained from chemical, radiolytic, and anodic oxidation of 3-methylindole and claimed to be a hexahydrofurodiindole of undefined stereochemistry (meso versus d,l). Single-crystal X-ray diffraction analysis of the compound, aimed at determining the stereochemistry, revealed that the actual product is an isomer, 7,8-dimethyl-2-oxa-4,11diazadibenzo[e,i ]tricyclo[5.4.0.0 3,8 ]undecane that derives from hydrolytic reorganization of the initially formed biindoline radical coupling product.