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Volumn 47, Issue 21, 2006, Pages 3607-3611

α-Alkoxystannanes as masked oxonium ions: application to the synthesis of furo[2,3-b]pyrans

Author keywords

Acetal; CAN; Oxidation; Oxonium; SET; Stannane

Indexed keywords

ALPHA ALKOXYSTANNANE; AMMONIUM NITRATE; CERIUM NITRATE; ORGANOTIN COMPOUND; PYRAN DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33748255752     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.161     Document Type: Article
Times cited : (7)

References (61)
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    • The oxidative cleavage of C-Sn bonds using CAN has precedent:. Hanessian S., and Ninkovic S. J. Org. Chem. 61 (1996) 5418-5424
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    • Other reagents have been utilized in C-Sn oxidations: Cr(VI)
    • Other reagents have been utilized in C-Sn oxidations: Cr(VI). Still W.C. J. Am. Chem. Soc. 99 (1997) 4836-4838
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    • + thereby changing the product distribution downstream of the fragmentation (see Fargeas, V.; Favresse, F.; Mathieu, D.; Beaudet, I.; Charrue, P.; Lebret, B.; Piteau, M.; Quintard, J.-P. Eur. J. Org. Chem. 2003, 1711-1721). We thank a referee for pointing out this possibility.{A figure is presented}
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    • and references cited therein
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    • note
    • -1;...
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    • This ring system is present in a number of natural products. For leading references see:
    • This ring system is present in a number of natural products. For leading references see:. Messer R., Schmitz A., Moesch L., and Häner R. J. Org. Chem. 69 (2004) 8558-8560
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    • note
    • cf. The following redox potentials:{A formula is presented}(Housecroft, C. E.; Sharpe, A. G. In Inorganic Chemistry; Pearson: Harlow, 2001; pp 613, 629).
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    • Competing intramolecuar Friedel-Crafts alkylation (see Fillion, E.; Beingessner, R. L. J. Org. Chem. 2003, 68, 9485-9488; Nagata, T.; Nakagawa, M.; Nishida, A. J. Am. Chem. Soc. 2003, 125, 7484-7485) was not observed.
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    • The electrochemical oxidation of α-alkoxygermanes has been reported:
    • The electrochemical oxidation of α-alkoxygermanes has been reported:. Yoshida J., Morita Y., Itoh M., Ishichi Y., and Isoe S. Synlett (1992) 843-844
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    • Hydride transfer from stannylcarbinols has been employed in the synthesis of acylstannanes:
    • Hydride transfer from stannylcarbinols has been employed in the synthesis of acylstannanes:. Marshall J.A., and Gung W.Y. Tetrahedron Lett. 30 (1989) 2183-2186
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    • An excellent review on this general area can be found in:
    • An excellent review on this general area can be found in:. Watt C.I.F. Adv. Phys. Org. Chem. 24 (1988) 57-112
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    • Watt, C.I.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.