2,3-Dihydrothiazol-2-ylidene

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 16, 1997, Pages 1709-1712

  Maier, Günther ^a   Endres, Jörg ^a   Reisenauer, Hans Peter ^a  

^a UNIVERSITY HOSPITAL GIESSEN   (Germany)

Author keywords

Carbenes; Decarboxylation; Heterocycles; Matrix isolation; Photochemistry

Indexed keywords

EID: 0030774602     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199717091     Document Type: Article

References (23)

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7. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
8. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
9. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
10. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
11. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
12. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
13. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
14. Review of nucleophilic carbenes. a) H.-W. Wanzlick, Angew. Chem. 1962, 74, 129-134; Angew. Chem. Int. Ed. Engl. 1962, 1, 75-80; b) M. Regitz, ibid. 1991, 103, 691-693 and 1991, 30, 674-676; ibid. 1996, 108, 791-79 and 1996, 35, 725-728; c) C. Köcher, W. A. Herrmann, ibid. 1997, 109, in press and 1997, 36, in press; d) see also [6, 7], and references therein.
15. D. Enders, K. Breuer, G. Raabe, J. Runsik, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem. 1995, 107, 1119-1121; Angew. Chem. Int. Ed. Engl. 1995, 34, 1021-1023.
16. D. Enders, K. Breuer, G. Raabe, J. Runsik, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem. 1995, 107, 1119-1121; Angew. Chem. Int. Ed. Engl. 1995, 34, 1021-1023.
17. A. J. Arduengo III, J. R. Goerlich, W. J. Marshall, Liebigs Ann./Receuil 1997, 365-374, also for a review of 2,3-dihydrothiazol-2-ylidenes. We thank Dr. Arduengo for a copy of this manuscript.
18. Synthesis: P. E. Iversen, Acta Chem. Scand. 1968, 22, 694-695.
19. Gaussian 94, revision B.1: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Alaham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Derees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian Inc., Pittsburgh, PA, USA, 1995.
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22. H. Schenkel, M. Schenkel-Rudin, Helv. Chim. Acta 1948, 31, 924-929.
23. Note added in proof (received on April 16, 1997): It has meanwhile been shown that 2 can be generated and detected by mass spectrometry in the gas phase (G. A. McGibbon, J. Hruscaronak, D. J. Lavarto, H. Schwarz, J. K. Terlouw, Chem. Eur. J. 1997, 3, 232-236).