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Volumn 9, Issue 9, 2007, Pages 1789-1792

Diazo preparation via dehydrogenation of hydrazones with "activated" DMSO

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; DIMETHYL SULFOXIDE; HYDRAZONE DERIVATIVE; HYDROGEN;

EID: 34248399249     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070515w     Document Type: Article
Times cited : (79)

References (31)
  • 4
    • 34248333317 scopus 로고    scopus 로고
    • Padwa, A, Pearson, W. H, Eds, John Wiley and Sons, Inc, New York
    • Mass, G. In Heterocyclic Compounds: 1,3-Dipolar Cycloaddition; Padwa, A., Pearson, W. H., Eds.; John Wiley and Sons, Inc.: New York, 2002; Vol. 59, pp 541-621.
    • (2002) Heterocyclic Compounds: 1,3-Dipolar Cycloaddition , vol.59 , pp. 541-621
    • Mass, G.1
  • 11
    • 4644339114 scopus 로고    scopus 로고
    • For recent nonheavy-metal-mediated hydrazone dehydrogenation methods, see: a
    • For recent nonheavy-metal-mediated hydrazone dehydrogenation methods, see: (a) Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc. 2004, 126, 12222-12223.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 12222-12223
    • Furrow, M.E.1    Myers, A.G.2
  • 13
    • 34248387592 scopus 로고    scopus 로고
    • For a summary of other oxidants that effect this conversion but find less use, see ref 7
    • For a summary of other oxidants that effect this conversion but find less use, see ref 7.
  • 16
    • 34248365527 scopus 로고    scopus 로고
    • The activation of DMSO with oxalyl chloride in THF was initially problematic. When DMSO was added to a precooled solution of oxalyl chloride in THF, the DMSO solidified and only slowly dissolved and reacted. This was circumvented by changing the order of addition: oxalyl chloride was added to a cold solution of DMSO in THF
    • The activation of DMSO with oxalyl chloride in THF was initially problematic. When DMSO was added to a precooled solution of oxalyl chloride in THF, the DMSO solidified and only slowly dissolved and reacted. This was circumvented by changing the order of addition: oxalyl chloride was added to a cold solution of DMSO in THF.
  • 17
    • 34248403591 scopus 로고    scopus 로고
    • Caution: Diazo compounds are known to be explosive, and ground glass is thought to catalyze the explosive decomposition of diazomethane. Although we had no explosions while working with these compounds, suitable safety precautions were taken and all manipulations were conducted behind safety blast shields
    • Caution: Diazo compounds are known to be explosive, and ground glass is thought to catalyze the explosive decomposition of diazomethane. Although we had no explosions while working with these compounds, suitable safety precautions were taken and all manipulations were conducted behind safety blast shields.
  • 20
    • 34248378613 scopus 로고    scopus 로고
    • Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. Organic Syntheses; Coll. 6, p 392 (1988); 50, p 50 (1970).
    • Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. Organic Syntheses; Coll. Vol. 6, p 392 (1988); Vol. 50, p 50 (1970).
  • 21
    • 34248359821 scopus 로고    scopus 로고
    • The apparatus and procedure we used to measure nitrogen gas evolution was based on that described by: (i) Holton, T. C. The Synthesis of Diazo Compounds by Low-Temperature Oxidation of Hydrazones with Lead Tetraacetate. Ph.D. Thesis, The Ohio State University, 1971, 98-102
    • The apparatus and procedure we used to measure nitrogen gas evolution was based on that described by: (i) Holton, T. C. The Synthesis of Diazo Compounds by Low-Temperature Oxidation of Hydrazones with Lead Tetraacetate. Ph.D. Thesis, The Ohio State University, 1971, 98-102.
  • 26
    • 34248351052 scopus 로고    scopus 로고
    • Smith, L. I.; Howard, K. L. Organic Syntheses; Coll. 3, p 351 (1955); 24, p 53 (1944).
    • Smith, L. I.; Howard, K. L. Organic Syntheses; Coll. Vol. 3, p 351 (1955); Vol. 24, p 53 (1944).
  • 27
    • 0032835068 scopus 로고    scopus 로고
    • Suzuki, T, Ohashi, K, Oriyama, T. Synthesis 1999, 1561-1563. The 13C NMR data for this compound are identical to those described in the literature. The 1H NMR data are also identical except for the chemical shift of one set of protons that appears to have been reported in error. We observed the methylene protons on the carbon bearing the ester as a triplet at 4.38 ppm. We believe the reported shift of 4.85 ppm is in error as it is presented out of numerical order in the original publication
    • 1H NMR data are also identical except for the chemical shift of one set of protons that appears to have been reported in error. We observed the methylene protons on the carbon bearing the ester as a triplet at 4.38 ppm. We believe the reported shift of 4.85 ppm is in error as it is presented out of numerical order in the original publication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.