Shorter and Easier Syntheses of Di??tert??butylketene and Related gem??Di??tert??butyl Compounds

R Knorr, KO Hennig, B Schubert…

Index: Knorr, Rudolf; Hennig, Karsten-Olaf; Schubert, Bernhard; Boehrer, Petra European Journal of Organic Chemistry, 2010 , # 34 p. 6651 - 6664

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Abstract

Abstract The ketene tBu 2 C= C= O is prepared from tBu 2 C= O in three steps (performable as a two-stage operation) through elimination of HCl from the intermediate product tBu 2 CCl– CH= O. The acid tBu 2 CH–CO 2 H, obtainable in two, three, or four preparative stages from tBu 2 C= O, adds slowly to the ketene to produce the anhydride (tBu 2 CH–CO) 2 O. Elemental lithium together with ClSiMe 3 converts tBu 2 CCl–CH= O into tBu 2 C= CH– ...