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Volumn 68, Issue 13, 2003, Pages 5013-5019

A new class of chiral organogermanes derived from C2-symmetric dithiols: Synthesis, characterization and stereoselective free radical reactions

Author keywords

[No Author keywords available]

Indexed keywords

GERMANIUM COMPOUNDS; HYDRIDES; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 0038209783     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026625s     Document Type: Article
Times cited : (20)

References (49)
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    • note
    • 3/t-BuOH/benzene/AIBN) was tested in the reduction of bromoadamantane. Gas chromatographic analysis of the reaction mixture after 1 h at 80 °C showed 99% yield of adamantane (using naphthalene as internal standard). Sodium cyanoborohydride alone does not reduce bromoadamantane under these conditions, therefore an organotin hydride formed in situ is probably the active reducing agent.
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    • note
    • 2 successfully afforded clean 2c.
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    • note
    • 1H NMR spectrum, which correlate with a singlet at 0.57 ppm (18H). This byproduct, probably the result of β-elimination at the germanium center with loss of isobutene, was never isolated and fully characterized, but it was found in small amounts in almost every reaction condition employed.
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    • (a) For a review of polarity-reversal catalysis of hydrogen abstraction reactions see: Roberts, B. P. Chem. Soc. Rev. 1999, 28, (b) Haque, M. B.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2881. (c) Haque, M. B.; Roberts, B. P. Tetrahedron Lett. 1996, 37, 9123.
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    • (a) For a review of polarity-reversal catalysis of hydrogen abstraction reactions see: Roberts, B. P. Chem. Soc. Rev. 1999, 28, (b) Haque, M. B.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2881. (c) Haque, M. B.; Roberts, B. P. Tetrahedron Lett. 1996, 37, 9123.
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    • note
    • 3SnH in the presence of variable amounts of
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    • -1a (from 0.1 up to 1 equiv). In all cases, the reduced product 16 was obtained as racemic, indicating that if 1a takes part in the hydrogen abstraction step it does so without any stereoselectivity. This is expected since the structure of 1a is not as rigid and sterically demanding as that of 7a.
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    • note
    • 3 resonances.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.