1-Vinyltricyclo[4.1.0.02,7]heptanes: Synthesis and Reactions with Electrophilic Dienophiles

✍ Scribed by Rüdiger Kreuzholz; Wolfgang Schmid-Vogt; Monika Maierhofer; Kurt Polborn; David S. Stephenson; Günter Szeimies

• Book ID: 102657800
• Publisher: John Wiley and Sons
• Year: 1998
• Tongue: English
• Weight: 935 KB
• Volume: 1998
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199801)1998:1<29::aid-ejoc29>3.0.co;2-q

✦ Synopsis

A series of 1-vinyltricyclo[4.1.0.0 2,7 ]heptanes 4 has been ob-and PTAD attacked the CC double bond forming a zwitterion, which in most cases underwent several carbenium ion tained by Ni 0 -catalyzed cross-coupling reactions of the corresponding Grignard reagent with vinyl halides or via reaction rearrangements until internal bond formation of the ionic centers took place. The main reaction path of DMAD and of 4b with various electrophiles. Selected model compounds 4 were treated with tetracyanoethylene (TCNE), N-phenyl-4 led via attack at the bicyclo[1.1.0]butane bridgehead to a biradical of type 38, which after H abstraction and CC bond 1,2,4-triazoline-3,5-dione (PTAD), and dimethyl acetylenedicarboxylate (DMAD). Product studies revealed that TCNE formation gave rise to the tricyclic system 37.