The reaction of sodium 3,6-di-tert-butyl-o-semiquinolate with Me3SiCl in THF leads to the formation of 2-(2′-trimethylsiloxy-3′,6′-di-tert-butylphenoxy)-2-trimethylsiloxy-3,6-di-tert-butylcyclohexadien-3,5-one 1. On the basis of IR and UV spectroscopy and analysis of the reaction products, it has been determined that the cyclohexadiene structure 1 is preserved on heating to moderate temperatures or on reaction with water or HCl, but photolysis leads to its decomposition, and so does reaction with metallic sodium or alkali. A scheme of the process is propounded.
This is a preview of subscription content, log in to check access.
Buy single article
Instant access to the full article PDF.
Price includes VAT for USA
Subscribe to journal
Immediate online access to all issues from 2019. Subscription will auto renew annually.
This is the net price. Taxes to be calculated in checkout.
G. A. Abakumov, V. A. Tsaryapkin, L. V. Gorbunova, and V. K. Cherkasov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1648 (1979).
B. L. Tumanskii, A. I. Prokof'ev, N. N. Bubnov, and S. P. Solodovnikov,Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 268 (1983).
K. Ley, E. Müller, and G. Schlechte,Chem. Ber.,90, 1530 (1957).
J. Petranek, J. Pilar, and D. Doskocilova,Tetrahedron Lett.,21, 1979 (1967).
K. Dimroth, H. Perst, K. Schlömer, K. Worschek, and K.-H. Müller,Chem. Ber.,100, 629 (1967).
A. J. Waring and H. Hart,J. Am. Chem. Soc.,86, No. 7, 1454 (1964).
E. Müller, A. Riecker, K. Scheffler, and A. Hoomayer,Angew. Chem.,78, 98 (1966).
Institute of Organometallic Chemistry, Russian Academy of Sciences, 603600 Nizhnii Novgorod. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 10, pp. 2385–2389, October, 1992.
About this article
Cite this article
Abakumov, G.A., Bayushkin, P.Y. & Filippova, E.I. Self-association of trimethylsilyl-3,6-di-tert-butyl-o-semiquinone. Russ Chem Bull 41, 1871–1874 (1992). https://doi.org/10.1007/BF00863825
- di-tert-butyl-substituted oxyphenoxylradicals
- cyclohexadiene structures
- geminal recombination reactions