Conclusions
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1.
The fluorodeoxygenation of (S)-proline by the action of sulfur tetrafluoride in hydrogen fluoride to (-)-2-trifluoromethylpyrrolidine was realized without affecting the carbon of the chiral center.
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2.
According to PMR data, 2-trifluoromethylpyrrolidine, its N-chloro derivative, and 1-chloro-2-methoxycarbonylpyrrolidine exist preferentially in the conformation with the pseudoequatorial orientation of the substituent at position 2.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1606–1612, July, 1988.
The authors are grateful to A. V. Ruban and V. A. Romanenko (institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR) for assistance in the fluorodeoxygenation of proline.
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Shustov, G.V., Denisenko, S.N., Chervin, I.I. et al. Fluorodeoxygenation of proline, optically active 2-trifluoromethylpyrrolidine, and its chromophoric derivatives. Russ Chem Bull 37, 1422–1427 (1988). https://doi.org/10.1007/BF00962755
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DOI: https://doi.org/10.1007/BF00962755