Syntheses and Reactions of Alkylthio- and Arylthio-Substituted 1,6-Methano[10]annulenes

✍ Scribed by Amanda C. Bryant-Friedrich; Richard Neidlein

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: German
• Weight: 740 KB
• Volume: 80
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19970800113

✦ Synopsis

Dedicated to Professor Mirhoel Hunack on the occasion of his 65th birthday (1 6.VII. 96)

The treatment of bromo-substituted 1,6-methano[lO]annulenes with sodium thiolates in DMF provides easy access to alkylthio-and arylthio-substituted 1,6-methano[l0]annulenes (Schemes 2 4 ) . These compounds are then brominated with N-bromosuccinimide (NBS) to study their reactivity in electrophilic substitution reactions (Schemes 5 and 6 ) . The resulting brominated thio-l,6-methano[lO]annulenes are, in a subsequent reaction, subjected to Heck coupling with (4-nitropheny1)acetylene (13) to produce the alkynylated derivatives 14 in reasonable yield (Scheme 7).