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1 article(s) from Atmaca, Ufuk

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

Esra Demir,
Ozlem Sari,
Yasin Çetinkaya,
Ufuk Atmaca,
Safiye Sağ Erdem and
Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

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Scheme 1: Oxazolidinone (1), five-membered cyclic carbonate (2) and some important compounds containing an ox...

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Scheme 2: Proposed mechanisms by Keshava Murthy and Dhar [41] and De Meijere and co-workers [42].

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Figure 1: Possible pathways for the formation of oxazolidinone intermediates 10 and 11. Optimized transition ...

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Figure 2: Potential energy profile related to the formation of oxazolidinone intermediates 10 and 11 at the P...

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Figure 3: IRC calculated for the formation of (a) 10 and (b) 11 at M06-2X/6-31+G(d,p) level. I-1, I-15, I-35, ...

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Figure 4: Optimized geometries for the stationary points for the formation of 10 at PCM(DCM)/M06-2X/6-31+G(d,...

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Scheme 3: Proposed mechanisms for the formation of oxazolidinone 9f.

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Figure 5: Potential energy profiles for paths 1a (blue), 1b (red), 2 (green) and relative Gibbs free energies...

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Figure 6: Optimized geometries for the stationary points of path 1b at PCM(DCM)/M06-2X/6-31+G(d,p)//M06-2X/6-...

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Scheme 4: Proposed mechanism for the formation of five-membered cyclic carbonate 8f.

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Figure 7: Potential energy profile and relative Gibbs free energies (kcal/mol) in DCM related to the formatio...

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Figure 8: Optimized geometries for the stationary points of step 1 for the formation of 16 at PCM(DCM)/M06-2X...

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Figure 9: Optimized geometries for the stationary points of step 2 for the formation of 17 at PCM(DCM)/M06-2X...

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Figure 10: Optimized geometries for the stationary points of step 3 for the formation of PC8 at PCM(DCM)/M06-2...

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Published 21 Jul 2020

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