Reaction of the Silver Salts of Arylnitroacetonitriles with 9-Bromofluorene Synthesis of 9-(α-Cyanoarylidene)fluorenes
✍ Scribed by Lianis, Pygmalion S. ;Rodios, Nestor A. ;Alexandrou, Nicholas E.
- Book ID
- 102367585
- Publisher
- John Wiley and Sons
- Year
- 1987
- Tongue
- English
- Weight
- 428 KB
- Volume
- 1987
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
The silver salts la-d react with 9-bromolluome to give both Cand 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.
The reaction of nitronate anions'' with several alkylating reagents is of special importance from synthetic and mechanistic aspect *I. Kurosawa et aL3) report on the synthesis of C-alkylation products in the reaction of nitronate ions with organothallium(II1) compounds, and a mechanistic study on a non-chain radicaloid Calkylation of some nitronate anions is presented by Katritzky et aI. ' 1. 2a -d (C-product) T 4a-d (80%)
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