Novel tocopheryl compounds XXIV. Studies into the nitrosation chemistry of γ-tocopherol: preparation of 5-nitroso-γ-tocopherol via an organomercury derivative of vitamin E

5-Nitroso-γ-tocopherol (5) was synthesized from γ-tocopherol (3) by aprotic nitrosation of an organomercurial intermediate (11). Under protic conditions the tautomeric ortho-benzoquinone monoxime (6) dominated over nitrosophenol 5.