Reaction of the Silver Salts of Arylnitroacetonitriles with 9‐Bromofluorene Synthesis of 9‐(α‐Cyanoarylidene)fluorenes

Abstract

The silver salts la-d react with 9-bromolluome to give both C-and 0-alkylated products 2 and 3. The latter decompose to yield 9-fluorenone and the a-cyanooximes 5. The products 2 upon treatment with NaOH/EtOH eliminate HN02 to a o r d 9-(a-cyanoarylidene)nuorenes 4 in 80% yield. 9-Chloro-9-phe nylfluorene reacts with the salt l a to give only the C-alkylatcd product 6 in 70% yield.

Generation and Reaction of Ammonium Ylides in Basic Two‐Phase Systems

“…The reactivity of the salts depends on the nature of the substituents present in the para position of phenyl ring. Thus, salt 2b, which possesses an electron-donating methoxy group, reacts with all the above-mentioned electrophiles to give cyclopropanes 4ba-bc,be-bg (Table 1), cyanoalkenes 8ba and 8bd [32] (Table 2), vinylcyclopropane 9b (Scheme 5), oxiranes 12ba and 12bc (Table 3) and dicyanostilbene 10b [52] (Scheme 6), usually in good yield. On the other hand, salt 2c, which is substituted with an electron-withdrawing cyano group, reacts only with electrophilic alkenes to give the cyclopropanes 4ca-cc,ce-cg in moderate yield ( Table 1).…”