Preferential attack of oxygen at o-position of t-butylated phenols in base catalyzed oxygenation

✍ Scribed by Akira Nishinaga; Toshio Itahara; Teruo Matsuura

• Book ID: 104243316
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 115 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92197-5

✦ Synopsis

Bewived in Japan 1 Ootobor 1974; rooeived in UK for publioation 11 mvember 1974) In the oxygenation of 2,6-di-t-butyl-4-alkylphenols in aqueous and alcoholic alkaline solutions normally P-position of the phenols is attacked by oxygen primarily to give 4-hydroxy-2,5-cyclohexadienone derivatives, 192 of which dissociated forms (peroxy anions) undergo intramolecular decomposition in DMP, DMSO, or HMPA containing ButOK to afford 4-hydroxy-5,6-epoxy-2cyclohexenones (epoxy-P-quinols).

3 We now find that the oxygenation of t-butylated phenols in ButOH containing ButOK unexpectedly leads to the preferential attack of oxygen at g-position of the phenols.

When oxygen was bubbled through a solution of 2,4,6-tri-t-butylphenol in ButOH containing Bu~OK at room temperature, one of O2 was taken up within 4 hr. The reaction mixture was diluted