Generation and trapping of a caged cyclopentylidenecarbene

Tetrahedron Letters

Volumn 37, Issue 4, 1996, Pages 467-470

  Marchand, Alan P ^a   Kumar, Kaipenchery A ^a   Rajagopal, D ^a   Eckrich, Ralf ^a   Bott, Simon G ^a  

^a UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030050189     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02200-7     Document Type: Article

References (12)

1. (a) Fitjer, L.; Kliebisch, U.; Wehle, D.; Modaressi, S. Tetrahedron Lett. 1982, 23, 1661.
2. (b) Gilbert, J. C.; Baze, M. E. J. Am. Chem. Soc. 1984, 106, 1885.
3. (c) Gilbert, J. C.; Giamalva, D. H. J. Org. Chem. 1992, 57, 4185.
4. (d) Gilbert, J. C.; Kirschner, S. Tetrahedron Lett. 1993, 34, 599, 603.
5. (a) Erickson, K. L.; Wolinsky, J. J. Am. Chem. Soc. 1965, 87, 1142.
6. (b) Similarly, ultrasonicated reaction of dibromomethylenecyclopentane with Li in THF in the presence of cyclohexene has been reported to afford 5 in 67% yield. See: Xu, L.; Lin, G. Tao, F.; Brinker, U. H. Acta Chem. Scand. 1992, 46, 650. We thank a referee for calling this publication to our attention.
7. w = 0.0699. A complete description will be given in the full paper.
8. 5,9]undecan-8-one; see: Flippen-Anderson, J. L.; Gilardi, R.; George, C.; Marchand, A. P.; Jin, P.-W.; Deshpande, M. N. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1988, C44, 1617.
9. We thank Professor John C. Gilbert, Department of Chemistry, University of Texas at Austin, for having provided a generous sample of DAMP for our use.
10. All calculations were performed by using SPARTAN software on an SGI INDIGO2 platform (UNIX operating system). Full geometry optimizations were performed at semiempirical (AM1) and ab initio [HF/3-21(G*) and HF/6-31(G*)] levels. Vibrational frequency calculations were used to characterize the first-order transition state (single imaginary frequency). SPARTAN computer software (version 4.0.3) was purchased from Wavefunction, Inc., 18401 von Karman, Suite 370, Irvine, CA 92715.
11. (a) Tseng, J.; McKee, M.; Shevlin, P. B. J. Am. Chem. Soc. 1987, 109, 5474.
12. (b) Johnson, R. P.; Daoust, K. J. J. Am. Chem.Soc. 1995, 117, 362.