Synthesis of ω-Nitro Acids and ω-Amino Acids by Ring Cleavage of α-Nitrocycloalkanones

✍ Scribed by Roberto Ballini; Fabrizio Papa; Corrado Abate

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 128 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199901)1999:1<87::aid-ejoc87>3.0.co;2-m

✦ Synopsis

Water / α-Nitrocycloalkanones / ω-Nitro acids / Surfactant

The reaction of various α-nitrocycloalkanones 1 with of the latter with HCOONH 4 /Pd-C, in methanol, at 80 °C affords ω-amino acids 3. The synthesis of methyl 9-aqueous 0.05 M NaOH, at 80 °C, in the presence of cetyltrimethylammonium chloride (CTACl) as a cationic oxodecanoate ( 8) is also reported. surfactant, produces ω-nitro acids 2 in good yields. Reduction

Given the well-known chemical differences between of gardless of the ring size. Only α-nitrocyclooctanone (1d) produces a mixure of unidentified products. the carbonyl group and the carbonϪnitro group moiety, their juxtaposition on two adjacent positions offers an im-Table 1. ω-Nitro acids 2 portant reactivity pattern, peculiar to α-nitro ketones. In fact the CϪC bond between the carbonyl group and the entry n R R 1 reaction time [h] yield [%] of 2 nitro-substituted atom of cyclic α-nitro ketones undergoes a 0 H H 3 9 0 cleavage by nucleophilic agents and this retro Claisen reac-