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Volumn 74, Issue 24, 2009, Pages 9501-9504

An expeditious entry to benzylic and allylic sulfones through byproduct-catalyzed reaction of alcohols with sulfinyl chlorides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; BENZYLIC; CATALYZED REACTIONS; CHEMICAL EQUATIONS; NEW PROTOCOL;

EID: 73149122781     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901974h     Document Type: Article
Times cited : (69)

References (42)
  • 1
    • 73149119863 scopus 로고    scopus 로고
    • For reviews, see: (a) Simpkins, N. S. Sulfones in Organic Synthesis; Pergamon Press: New York, 1993.
    • For reviews, see: (a) Simpkins, N. S. Sulfones in Organic Synthesis; Pergamon Press: New York, 1993.
  • 4
    • 73149110665 scopus 로고    scopus 로고
    • Neamati, N.; Kabalka, G. W.; Venkataiah, B.; Dayam, R. WO2007081966, 2007.
    • Neamati, N.; Kabalka, G. W.; Venkataiah, B.; Dayam, R. WO2007081966, 2007.
  • 5
    • 0001097869 scopus 로고
    • For a review, see:, Trost, B. M, Fleming, I, Eds, Pergamon Press: Oxford
    • For a review, see: Solladie, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 133.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 133
    • Solladie, G.1
  • 14
    • 73149096337 scopus 로고    scopus 로고
    • v. Braun, J.; Weissbach, K. Ber. 1930, 63B, 2836. The authors mentioned a warm reaction mixture but did not specify the temperature.
    • v. Braun, J.; Weissbach, K. Ber. 1930, 63B, 2836. The authors mentioned a warm reaction mixture but did not specify the temperature.
  • 20
    • 0001175964 scopus 로고
    • For the preparation of sulfinyl chlorides, see: a
    • For the preparation of sulfinyl chlorides, see: (a) Whitesell, J. K.; Wong, M.-S. J. Org. Chem. 1991, 56, 4552.
    • (1991) J. Org. Chem , vol.56 , pp. 4552
    • Whitesell, J.K.1    Wong, M.-S.2
  • 22
    • 73149083111 scopus 로고    scopus 로고
    • This reaction was carried out on a 0.25-mmol scale, and the yield was improved to 87% when performing the reaction on a 10-mmol scale
    • This reaction was carried out on a 0.25-mmol scale, and the yield was improved to 87% when performing the reaction on a 10-mmol scale.
  • 28
    • 73149108917 scopus 로고    scopus 로고
    • At an early stage of the reaction, a significant portion of alcohol was converted to the corresponding ether that could serve as another source for carbocation B under acidic conditions. For a relevant study, see ref 8c
    • 8c.
  • 29
    • 36849062647 scopus 로고    scopus 로고
    • For some recent examples of the acidic byproduct co-catalyzed reactions, see: a
    • For some recent examples of the acidic byproduct co-catalyzed reactions, see: (a) Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2007, 9, 4931.
    • (2007) Org. Lett , vol.9 , pp. 4931
    • Nishimoto, Y.1    Yasuda, M.2    Baba, A.3
  • 36
    • 34347262098 scopus 로고    scopus 로고
    • For reviews of such highly functionalized alcohols, see: a
    • For reviews of such highly functionalized alcohols, see: (a) Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 4614
    • Masson, G.1    Housseman, C.2    Zhu, J.3
  • 38
    • 73149109791 scopus 로고    scopus 로고
    • Benzenesulfinic acid could also be generated through the decomposition of benzenesulfinyl chloride with moisture
    • Benzenesulfinic acid could also be generated through the decomposition of benzenesulfinyl chloride with moisture.
  • 40
    • 37049073435 scopus 로고    scopus 로고
    • Our results are inconsistent with the [2,3]-sigmatropic rearrangement of an allylic sulfinate, which should favor the formation of allylic sulfone 5 (R1, H) rather than its stereoisomer 6 (R 1, H, For the rearrangement of allylic sulfinates to yield allylic sulfones, see: (a) Knight, D. J, Whitham, G. H, Williams, J. G. J. Chem. Soc, Perkin Trans. 1 1987, 2149
    • 1 = H). For the rearrangement of allylic sulfinates to yield allylic sulfones, see: (a) Knight, D. J.; Whitham, G. H.; Williams, J. G. J. Chem. Soc., Perkin Trans. 1 1987, 2149.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.