The Simplest, Isolable, Alkynyl Isocyanate HC/CNCO: Synthesis and Characterization
Yuanyuan Qin1,+ , Bo Lu1,+ , Guntram Rauhut2, Manfred Hagedorn3, Klaus Banert3, Chao Song1, Xianxu Chu1, Lina Wang4, and Xiaoqing Zeng1, 4,*（曾小庆）
1College of Chemistry, Chemical Engineering and Materials Science, Soochow University Suzhou 215123 (China)
2 Institute for Theoretical Chemistry, University of Stuttgart Pfaffenwaldring 55, Stuttgart 70569 (Germany)
3Chemnitz University of Technology, Organic Chemistry Strasse der Nationen 62, Chemnitz 09111 (Germany)
4 Department of Chemistry, Fudan University Shanghai 200433 (China)
+ These authors contributed equally to this work.
Angew. Chem. Int. Ed. 2019, 58, 17277--17281
Alkynyl isocyanates have been postulated as highly reactive intermediates in synthetic chemistry. Herein, the parent molecule HC/CNCO is isolated for the first time. In sharp contrast to the previously reported short lifetime (ca. 15 s) at room temperature, we found that HC/CNCO has a lifetime of 55 h in the gas phase (2 mbar, 300 K) with a melting point of @79.5 8C and vaporization enthalpy (DHvap) of 23.1- (1) kJmol@1 . Apart from the IR (gas, solid, and matrix), 1H and 13C NMR, and UV/Vis spectroscopic characterization, its photoisomerization with a acylnitrene HC/CC(O)N and cyanoketene NCC(H)CO has been observed.