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Volumn 48, Issue 35, 2007, Pages 6150-6154

Simple and efficient deprotection of 1,3-dithianes and 1,3-dithiolanes by copper(II) salts under solvent-free conditions

Author keywords

Cleavage; Copper(II) salts; Oxidation; Solid state synthesis; Thioacetals; Ultrasound

Indexed keywords

1,3 DITHIANE DERIVATIVE; 1,3 DITHIOLANE DERIVATIVE; CUPRIC ION; MONTMORILLONITE; SODIUM CHLORIDE;

EID: 34547453814     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.160     Document Type: Article
Times cited : (17)

References (54)
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    • Tierney J.P., and Lidstrom P. (Eds), Blackwell, Oxford, UK
    • In: Tierney J.P., and Lidstrom P. (Eds). Microwave Assisted Organic Synthesis Vol. 280 (2005), Blackwell, Oxford, UK 89
    • (2005) Microwave Assisted Organic Synthesis , vol.280 , pp. 89
  • 40
    • 34547409416 scopus 로고    scopus 로고
    • note
    • This procedure avoids a previous synthesis of Claycop.
  • 41
    • 34547450224 scopus 로고    scopus 로고
    • note
    • 3 supported on K10 (Clayan) has been reported as a reagent for deprotection of thioacetals and thioketals, using a ratio substrate/Clayan of 1:7 (Ref. 7).
  • 43
    • 34547413589 scopus 로고    scopus 로고
    • note
    • 2 (0.1 equiv) as co-oxidant to perform the cleavage of thiolane 1a yielding similar results.
  • 44
    • 0009143710 scopus 로고    scopus 로고
    • Renaud P., and Sibi M. (Eds), Wiley-VCH Verlag GmbH, Weinheim
    • Linker T. In: Renaud P., and Sibi M. (Eds). Radicals in Organic Synthesis Vol. 1, Chapter 2.4 (2001), Wiley-VCH Verlag GmbH, Weinheim 219-228
    • (2001) Radicals in Organic Synthesis , vol.1 Chapter 2.4 , pp. 219-228
    • Linker, T.1
  • 48
    • 34547429618 scopus 로고    scopus 로고
    • note
    • The deprotection of the 1,3-dithiolane derivative from the cinnamaldehyde affords a mixture of cinnamaldehyde and benzaldehyde. The oxidative cleavage of the cinnamaldehyde by Cu(II) was not avoided even at shorter reaction times.
  • 49
    • 34547400653 scopus 로고    scopus 로고
    • note
    • ox (TMB) = 0.77 V, versus SCE in MeCN (Ref. 5).
  • 50
    • 0000902668 scopus 로고
    • -, followed by ET to produce a sulfur radical cation. Further electrochemical studies are required to elucidate the role of nitrate
    • -, followed by ET to produce a sulfur radical cation. Bosch E., and Kochi J. J. Org. Chem. 60 (1995) 3172-3183 Further electrochemical studies are required to elucidate the role of nitrate
    • (1995) J. Org. Chem. , vol.60 , pp. 3172-3183
    • Bosch, E.1    Kochi, J.2
  • 51
    • 34547428098 scopus 로고    scopus 로고
    • 2 atmosphere Kamata, M.; Kato, Y.; Hasegawa, E. Tetrahedron Lett. 1991, 32, 4349-4352; whereas pathway (b) has been suggested for the dethioacetalization induced by visible light and dyes (Epling, G. A.; Wang, Q. Tetrahedron Lett. 1992, 33, 5909-5912) and indirect electrochemical oxidation, (Platen, M.; Steckhan, E. Tetrahedron Lett. 1980, 21, 511-514).
  • 52
    • 34547475157 scopus 로고    scopus 로고
    • note
    • Another possibility would be a fast interconversion between the two distonic radical cations 10 and 8, the former a carbocation with a thiyl radical, and the latter a carbon radical with a sulfur cation moiety.
  • 53
    • 34547417189 scopus 로고    scopus 로고
    • note
    • 5 requires an excess of the oxidant. Thus, the mechanism proposed to account for this dethioacetalization involves one-electron oxidation of a sulfur radical to a sulfonium ion as a key step. This intermediate by a second oxidative ET process affords a dication responsible for the formation of the ketone. Refs. 11 and 5.
  • 54
    • 34547427535 scopus 로고    scopus 로고
    • note
    • 3, 30 °C): δ = 25.1, 25.7, 26.0, 29.9, 31.4, 38.3, 40.3, 48.0, 57.5, 67.7.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.