Table of Contents
Research Letters in Organic Chemistry
Volume 2008, Article ID 742590, 4 pages
Research Letter

A Novel Dimer of 𝛼 -Tocopherol

1Department of Chemistry, University of Natural Resources and Applied Life Sciences (BOKU), Muthgasse 18, 1190 Vienna, Austria
2Dipartimento di Chimica e Chimica Industriale, UniversitΓ  di Pisa, Via Risorgimento 35, 56126 Pisa, Italy
3Research and Development, DSM Nutritional Products Ltd., P.O. Box 3255, 4002 Basel, Switzerland

Received 26 June 2008; Accepted 2 August 2008

Academic Editor: Kazuaki Ishihara

Copyright © 2008 Anjan Patel et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Decomposition of the complex 4, formed between the 𝛼 -tocopherol ortho-quinone methide (2) and NMMO, by fast heating from βˆ’ 7 8 ∘ C to 7 0 ∘ C in inert solvents produces a novel 𝛼 -tocopherol dimer with 6 𝐻 , 1 2 𝐻 -dibenzo[b,f][1,5]dioxocine structure (5) which—in contrast to the well-known spiro-dimer of 𝛼 -tocopherol (3)—is symmetrical. This is the first example of a direct reaction of the highly transient zwitterionic, aromatic precursor 2a in the formation of the ortho-quinone methide 2.