Sulfonyl-Activated Cyclobutenes as Building Blocks for the Synthesis of Dihydrodiazepines

✍ Scribed by Landen, Harald ;Martin, Hans-Dieter ;Steigel, Alois

• Publisher: Wiley (John Wiley & Sons)
• Year: 1987
• Tongue: English
• Weight: 467 KB
• Volume: 120
• Category: Article
• ISSN: 0009-2940
• DOI: 10.1002/cber.19871200208

✦ Synopsis

Bis(phcnylthio)-I-cyclobutcnc (S), prepared in high yield using a modified literature procedure, was oxidized to the corresponding his-sulfone 2. sulfone-sulfoxide 9, bis-sulfoxide 10, or monosulfoxidc 15 by means of hydrogen peroxide or sodium periodate, rcspectivcly. When treated with diazomethane the bis-sulfone 2 and thc sulfonc-sulroxidc 9 yicld thc dihydrodiazcpincs 4 a and 11, rcspcctivcly. Thc rcactivity of thcse cyclobutenes and thc rcgioselectivity of 9 is discussed in terms of the MNDO model.