Cyclic 1,3-dipoles or acyclic phosphonium ylides? Electronic characterization of "Montréalones"

Journal of the American Chemical Society

Volumn 130, Issue 31, 2008, Pages 10052-10053

  Krenske, Elizabeth H ^a   Houk, K N ^a   Arndtsen, Bruce A ^b   St Cyr, Daniel J ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC PHOSPHONIUM YLIDE; CHEMICAL COMPOUND; CYCLIC 1,3 DIPOLE; MONTREALONE; PHOSPHONIUM DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL MODEL; CYCLOADDITION; ELECTRONICS; GEOMETRY; ISOMER;

EID: 48749109826     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802646f     Document Type: Article

References (14)

1. St. Cyr, D. J.; Arndtsen, B. A. J. Am. Chem. Soc. 2007, 129, 12366.
2. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899.
3. Baker, W.; Ollis, W. D. Q. Rev. Chem. Soc. 1957, 1, 15.
4. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Angew. Chem., Int. Ed. Engl. 1964, 3, 136.
5. (a) Ramirez, F.; Madan, O. P.; Heller, S. R. J. Am. Chem. Soc. 1965, 87, 731.
6. (b) Bentrude, W. G.; Johnson, W. D.; Khan, W. A. J. Am. Chem. Soc. 1972, 94, 923.
7. (c) Castelijns, M. M. C. F.; Schipper, P.; van Aken, D.; Buck, H. M. J. Org. Chem. 1981, 46, 47.
8. Thalji, R. K.; Roush, W. R. J. Am. Chem. Soc. 2005, 127, 16778.
9. Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
10. Bylaska, E. J. NWChem, version 5.0; Pacific Northwest National Laboratory: Richland, WA, 2006.
11. -1 in most cases.
12. 3 and a cyc structure for PPh(catechyl) (Arndtsen and St. Cyr, unpublished data).
13. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646.
14. Knorr, R.; Huisgen, R.; Staudinger, G. K. Chem. Ber. 1970, 103, 2639-2646.