Pronounced Steric Hindrance for Nitrogen Inversion in 1,3,4-Oxadiazolidines
Remir G. Kostyanovsky Prof.
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorGulnara K. Kadorkina Dr.
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorVasilii R. Kostyanovsky
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorVolker Schurig Prof. Dr.
University of Tübingen Institute of Organic Chemistry 72076 Tübingen (Germany) Fax: (+49) 7071-29-5538
Search for more papers by this authorOliver Trapp Dipl.-Chem.
University of Tübingen Institute of Organic Chemistry 72076 Tübingen (Germany) Fax: (+49) 7071-29-5538
Search for more papers by this authorRemir G. Kostyanovsky Prof.
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorGulnara K. Kadorkina Dr.
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorVasilii R. Kostyanovsky
N.N. Semenov Institute of Chemical Physics Russian Academy of Sciences 117977 Moscow (Russian Federation) Fax: (+7) 095-938-2156/939-7417
Search for more papers by this authorVolker Schurig Prof. Dr.
University of Tübingen Institute of Organic Chemistry 72076 Tübingen (Germany) Fax: (+49) 7071-29-5538
Search for more papers by this authorOliver Trapp Dipl.-Chem.
University of Tübingen Institute of Organic Chemistry 72076 Tübingen (Germany) Fax: (+49) 7071-29-5538
Search for more papers by this authorAsymmetric Nitrogen, Part 83. This work was supported by the Russian Foundation for Basic Research (RFBR) (grant No. 97-03-33021) and DFG-RFBR (grant No. 98-03-04119). O.T. thanks the Fonds der Chemischen Industrie for a doctorate scholarship. Part 82: D. A. Lenev, K. A. Lyssenko, R. G. Kostyanovsky, Izv. Akad. Nauk. Ser. Khim. 2000, N7 [Russ. Chem. Bull. 2000, 49, in press].
Abstract
Very high inversion barriers for a pyramidal nitrogen atom have been found for the sterically hindered 1,2,4-oxadiazolidines 1 (R1, R2=CH3) and 2 (R1=COOCH3, R2=CH2CH3, only one enantiomer is shown). The synthesis and NMR studies of the diastereomerization of 2 are described, as well as the determination of the enantiomerization barrier of 1 by stopped-flow multidimensional gas chromatography (sfMDGC).
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