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Volumn 128, Issue 5, 2006, Pages 1605-1610

A comprehensive approach to the synthesis of sulfate esters

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 32244435187     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056086j     Document Type: Article
Times cited : (107)

References (28)
  • 2
  • 15
    • 0004275780 scopus 로고
    • Reactions of sulfonate and sulfate esters
    • Oae, S., Ed.; Plenum Press: New York
    • Kaiser, E. T. Reactions of Sulfonate and Sulfate Esters. In Organic Chemistry of Sulfur, Oae, S., Ed.; Plenum Press: New York, 1977; pp 649-679.
    • (1977) Organic Chemistry of Sulfur , pp. 649-679
    • Kaiser, E.T.1
  • 19
    • 33947295099 scopus 로고
    • Neopentyl and isobutyl chlorosulfate can be easily prepared in large scale by the reaction of the respective alcohols with sulfuryl chloride. The crude chlorosulfates can be distilled and then stored under argon at -20 °C for several months without detectable decomposition. Buncel, E. Chem. Rev. 1970, 70, 323-337.
    • (1970) Chem. Rev. , vol.70 , pp. 323-337
    • Buncel, E.1
  • 20
    • 32244438945 scopus 로고    scopus 로고
    • note
    • Initial reactions of phenol with neopentyl chlorosulfate in the presence of a tertiary amine base gave diester 1, but in unsatisfactory yields (<50%), even with reaction times of up to 3 days. Lithium aryloxides, produced using n-butyllithium or lithium bis(trimethylsilyl)amide, reacted slowly with neopentyl chlorosulfate. These reactions did not go to completion, even with extended reaction times.
  • 21
    • 32244448703 scopus 로고    scopus 로고
    • note
    • Multiple equivalents of isobutyl chlorosulfate were used to increase the reaction rate and protect the diester product from degradation under the reaction conditions. Lithium phenoxides reacted with isobutyl chlorosulfate to give isobutyl ethers almost exclusively.
  • 23
    • 32244431834 scopus 로고    scopus 로고
    • note
    • 1H NMR, IR, and MS.
  • 25
    • 32244435268 scopus 로고    scopus 로고
    • note
    • Triethylamine was used to keep the reaction mixture slightly basic and prevent decomposition of sulfate monoester products.
  • 27
    • 0043045262 scopus 로고
    • A similar result was observed in the solvolysis of the analogous p-bromobenzenesulfonate esters of tetrahydrofuran-2-methanol and tetrahydropyran-2-methanol. Kwiatkowski, G. T.; Kavarnos, S. J.; Closson, W. D. J. Heterocycl. Chem. 1965, 2, 11-14.
    • (1965) J. Heterocycl. Chem. , vol.2 , pp. 11-14
    • Kwiatkowski, G.T.1    Kavarnos, S.J.2    Closson, W.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.