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Volumn 71, Issue 15, 2006, Pages 5646-5657

Lithium carbenoids-ultra-reactive yet selective reagents for methylenation and halomethylenation of sulfones

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLSUBSTITUTED CARBENOID; METHYLENE CARBENOIDS; OLEFINATION; VINYLIDENE CARBENOIDS;

EID: 33746327490     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060669+     Document Type: Article
Times cited : (18)

References (82)
  • 1
    • 0000041741 scopus 로고
    • Part 3 of series entitled "Olefin Synthesis by Reaction of Stabilized Carbanions with Carbene Equivalents." (a) Part 1: Pearlman, B. A.; Putt, S. R.; Fleming, J. A. J. Org. Chem. 1985, 50, 3622.
    • (1985) J. Org. Chem. , vol.50 , pp. 3622
    • Pearlman, B.A.1    Putt, S.R.2    Fleming, J.A.3
  • 9
    • 0000833527 scopus 로고
    • Metalated sulfones tend to be "somewhat unreactive" toward alkylation: Magnus, P. D. Tetrahedron 1977, 33, 2019.
    • (1977) Tetrahedron , vol.33 , pp. 2019
    • Magnus, P.D.1
  • 10
    • 33746336798 scopus 로고    scopus 로고
    • U.S. Patent 4,549,030. Oct. 22, 1985. (Examples 11A and 18)
    • Pearlman, B. A. U.S. Patent 4,549,030. Oct. 22, 1985. (Examples 11A and 18).
    • Pearlman, B.A.1
  • 36
    • 33746342608 scopus 로고    scopus 로고
    • note
    • The digit after the decimal in the yields of olefin 2 is not significant. However, the digit after the decimal in the yields of the byproducts (7b, 4, 5, 6, and recovered 1) is significant. Thus, to maintain consistency of presentation, the digit after the decimal is reported for all yields. Note that 100% minus the yield of recovered sulfone 1 is used rather than the yield of olefin 2 in all selectivity calculations. Thus, the legitimacy of including the digit after the decimal is a moot point.
  • 37
    • 33746364323 scopus 로고    scopus 로고
    • note
    • See Supporting Information (Appendix) for derivation.
  • 40
    • 33746355078 scopus 로고    scopus 로고
    • note
    • 1/2 = (t ln(1/2))/(ln(l - M), where t is the time (in seconds) and M is the yield of olefin 2 (expressed in decimal format).
  • 41
    • 33746379408 scopus 로고    scopus 로고
    • note
    • 2 (34.3%).
  • 46
    • 33746338723 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the sulfinate elimination step (syn-coplanar or anti-periplanar) could also be deduced from the absolute configuration of the unreacted, kinetically resolved carbenoid.
  • 64
    • 33746362729 scopus 로고    scopus 로고
    • Rappoport, Z., Marek, I., Eds.; John Wiley and Sons: New York, Chapter 13
    • For two excellent recent reviews, see: (a) Braun, M. In The Chemistry of Alkyllithium Compounds; Rappoport, Z., Marek, I., Eds.; John Wiley and Sons: New York, 2004; Chapter 13, pp 829-900.
    • (2004) The Chemistry of Alkyllithium Compounds , pp. 829-900
    • Braun, M.1
  • 77
    • 33746365258 scopus 로고    scopus 로고
    • note
    • 2 that has been added.
  • 80
    • 33746376130 scopus 로고    scopus 로고
    • note
    • 11Br) could be detected in the crude reaction mixtures by GC. Therefore, no n-octane (product of the Wurtz-Fittig coupling between n-BuLi and n-BuBr) was formed under the conditions of the experiments, thus validating the use of n-octane as internal standard.
  • 82
    • 33746334283 scopus 로고    scopus 로고
    • note
    • 2, 20.13 min. cis- and trans-5-Decene were not sufficiently resolved to permit individual quantitation. Response factors were determined for each component by injection of pure samples purchased from commercial supply houses.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.