Substitution vs. reduction of benzyl halides with thiol and selenol nucleophiles

✍ Scribed by L. Hevesi

• Book ID: 104212648
• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 222 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)71001-x

✦ Synopsis

This work was induced by observations made during our research on isoalloxasines'.

For comparison purposes we wanted to prepare 8a-cysteinyl 3,10-dimethylisoalloxazine by treating 8a-2 bromo 3,lO dimethylisoalloxazine 1 with L-cysteine hydrochloride in DMF (room temperature, 70h) . -

We were surprised to find thattbesides unreacted r, the only isolable product was 3,8,10-trimethylisoalloxazine 2 : no appreciable if any substitution oocured on the benzylic carbon.