15N-labelling studies of the reaction of 2,6-di-t-butyl-4-methyl-4-nitrocyclohexa-2,5-dienone with nitrogen dioxide; A revised mechanism

✍ Scribed by Michael P. Hartshorn; Richard G. Jensen; A.Grant Waller; Graeme J. Wright

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 241 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)96950-8

✦ Synopsis

16 h gives the 4,5,6-trinitro ketone (2), labelled (15N02) at C6 but not at C4, and recovered 4-nitrodienone (1) in which extensive loss of 15N02 has occurred. The mechanistic implications of these and related results are discussed. Reaction Of 2,6-di-t-butyl-4-methylphenol (3) with excess nitrogen dioxide in benzene gives initially the 4nitrodienone (1) which undergoes further slow addition (c. 15% complete after 16 h) of nitrogen dioxide to yield 2,6-di-t-butyl-4-methyl-r-4,c-5,c-6-trinitrocyclohex-2-enone