Notiz über die Reaktion von Phosphortrichlorid(bromid) und Thionylchlorid(bromid) mit Formamiden zu Carbamidsäurechloriden(bromiden)

Schindler, Norbert; Plöger, Walter

doi:10.1002/cber.19711040340

Cited by 14 publications

(2 citation statements)

References 5 publications

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“…The ATR-IR spectrum is provided in Figure S26 (Supporting Information). The precursor for the azide, dimethylcarbamoyl chloride, was synthesized according to a published method, 12 and all other starting materials were commercial products.…”

Section: ■ Conclusionmentioning

confidence: 99%

Photolysis of Dimethylcarbamoyl Azide in an Argon Matrix: Spectroscopic Identification of Dimethylamino Isocyanate and 1,1-Dimethyldiazene

et al. 2013

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The UV photolysis of dimethylcarbamoyl azide has been investigated in an argon matrix at cryogenic temperatures. The products of the photolysis were identified by infrared spectroscopy supported by quantum-chemical calculations. Sequential formation of dimethylamino isocyanate (Me2N-NCO), 1,1-dimethyldiazene (Me2N═N), and ethane was established. Therefore, the major decomposition channel is identified as Me2NC(O)N3 → Me2N-NCO → Me2N═N → Me-Me, via consecutive N2, CO, and N2 eliminations. Ground-state geometries, vibrational frequencies, IR intensities, and UV excitation energies of the transient dimethylamino isocyanate and 1,1-dimethyldiazene have been computed using the B3LYP and SAC-CI methods and the aug-cc-pVTZ basis set.

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Section: ■ Conclusionmentioning

confidence: 99%

Photolysis of Dimethylcarbamoyl Azide in an Argon Matrix: Spectroscopic Identification of Dimethylamino Isocyanate and 1,1-Dimethyldiazene

et al. 2013

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“…Whilst reaction of DMF with chlorinating agents to give DMCC is known, the lack of obvious references to the potential toxicological concerns associated with use of DMF as a catalyst for chlorination reactions suggests that the potential for generation of DMCC as a toxic by-product from such reactions may not be generally appreciated.…”

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confidence: 99%

Potential Toxicological Concerns Associated with Carboxylic Acid Chlorination and Other Reactions

Levin

1997

Org. Process Res. Dev.

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Enantioselective Lithiation and Substitution of (E)-CinnamylN,N-Diisopropylcarbamate through Use of (−)-Sparteine Complexes

et al. 1998

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The title reaction leads to diastereomeric lithium carbanion pairs that are configurationally unstable and equilibrate even at temperatures below –50 °C. The initially formed epimer (1S)‐epi‐10 is rapidly converted to the thermodynamically more stable (1R)‐10 (in toluene solution). Carboxylation, acylation with acid chlorides, stannylation, and silylation take place at the α‐position with stereoinversion (79‐86% ee). Methylating agents attack the γ‐position; here, the stereochemical course depends on the leaving group, anti‐SE′ for the iodide (50% ee) and syn‐SE′ (48% ee) for the tosylate.

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Notiz über die Reaktion von Phosphortrichlorid(bromid) und Thionylchlorid(bromid) mit Formamiden zu Carbamidsäurechloriden(bromiden)

Cited by 14 publications

References 5 publications

Photolysis of Dimethylcarbamoyl Azide in an Argon Matrix: Spectroscopic Identification of Dimethylamino Isocyanate and 1,1-Dimethyldiazene

Photolysis of Dimethylcarbamoyl Azide in an Argon Matrix: Spectroscopic Identification of Dimethylamino Isocyanate and 1,1-Dimethyldiazene

Potential Toxicological Concerns Associated with Carboxylic Acid Chlorination and Other Reactions

Enantioselective Lithiation and Substitution of (E)-CinnamylN,N-Diisopropylcarbamate through Use of (−)-Sparteine Complexes

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