Rearrangement Kinetics of Spiropentylchlorocarbene, [3]Triangulylchlorocarbene, and Related Species

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1439-1442

  Moss, Robert A ^a   Zheng, Fengmei ^a   Krogh Jespersen, Karsten ^a  

^a RUTGERS UNIVERSITY   (United States)

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ARTICLE;

EID: 0037599764     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010023y     Document Type: Article

References (41)

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2. Moss, R. A. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press: Greenwich, CT, 1994; pp 59f.
3. (b) Regitz, M., Ed. Methoden Org. Chem. (Houben-Weyl), 4th ed. 1989, E19b.
4. (c) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971; Chapter 12.
5. (d) Jones, M., Jr., Moss, R. A., Eds. Carbenes; Wiley: New York, 1973; Vol. 1, Chapter 1.
6. Ho, G.-J.; Krogh-Jespersen, K.; Moss, R. A.; Shen. S.; Sheridan, R. S.; Subramanian, R. J. Am. Chem. Soc. 1989, 111, 6875.
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14. For an excellent review of oligospirocyclopropane systems, see: (a) de Meijere, A.; Kozhushkov, S. I. Chem. Rev. 2000, 100, 93. See also:
15. (b) Seebach, M. V.; Kozhushkov, S. I.; Boese, R.; Benet-Buchholz, J.; Yufit, D. S.; Howard, J. A. K.; de Meijere, A. Angew. Chem., Int. Ed. 2000, 39, 2495.
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17. Kuznetsova, T. S.; Kozhushkov, S. I.; Gromov, A. V.; Vatlina, L. P.; Kozlovskii, V. I.; Zefirov, N. S. J. Org. Chem. USSR (Engl. Trans.) 1992, 28, 256; Zh. Org. Khim. 1992, 28, 317.
18. de Meijere, A.; Kozhushkov, S. I. Unpublished results cited in ref 7a, p 126 and note 121.
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21. Köster, R.; Arora, S.; Binger, P. Synthesis 1971, 322. Caubere, P.; Coudert, G. Bull. Soc. Chim. France 1971, 2234.
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23. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969. Moss, R. A.; Ma, W.; Merrer, D. C.; Xue, S. Tetrahedron Lett. 1995, 36, 8761.
24. Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969. Moss, R. A.; Ma, W.; Merrer, D. C.; Xue, S. Tetrahedron Lett. 1995, 36, 8761.
25. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
26. Products 13-15 were previously known; see refs 8 and 9.
27. Reversed distributions appear in refs 7a and 8; the former (cited here) is correct: de Meijere, A. Private communication, 4 December, 2000.
28. 1H NMR.
29. See ref 2a, pp 66-67. (b) Nigam, M.; Platz, M. S.; Showalter, B. M.; Toscano, J. P.; Johnson, A.; Abbot, S. C.; Kirchoff, M. M. J. Am. Chem. Soc. 1998, 120, 8055 and references therein.
30. For a description of our LFP apparatus, see: Moss, R. A.; Johnson, L. A.; Merrer, D. C.; Lee, G. E., Jr. J. Am. Chem. Soc. 1999, 121, 5940.
31. Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595.
32. 3a very likely as a result of increased steric problems originating at the additional cyclopropyl unit of 5.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
34. Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
35. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. Pople, J. A.; Hariharan, P. C. Theor. Chim. Acta. 1973, 28, 213. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
36. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. Pople, J. A.; Hariharan, P. C. Theor. Chim. Acta. 1973, 28, 213. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
37. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. Pople, J. A.; Hariharan, P. C. Theor. Chim. Acta. 1973, 28, 213. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
38. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650. McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639. Pople, J. A.; Hariharan, P. C. Theor. Chim. Acta. 1973, 28, 213. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
39. Frisch, M. J. et al. Gaussian 98, revision A.5; Gaussian, Inc.: Pittsburgh, PA, 1998.
40. Steric effects are also central in the analogous rearrangements of 2,2-dimethylcyclopropylmethyicarbene: Bird, C. L.; Frey, H. M.; Stevens, I. D. R. Chem. Commun. 1967, 707. Stevens, I. D. R.; Frey, H. M.; Bird, C. L. Angew. Chem., Int. Ed. 1968, 7, 646.
41. Steric effects are also central in the analogous rearrangements of 2,2-dimethylcyclopropylmethyicarbene: Bird, C. L.; Frey, H. M.; Stevens, I. D. R. Chem. Commun. 1967, 707. Stevens, I. D. R.; Frey, H. M.; Bird, C. L. Angew. Chem., Int. Ed. 1968, 7, 646.