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Volumn 44, Issue 29, 2003, Pages 5381-5384

Borane-induced radical reduction of 1-alkenyl- and 1-alkynyl-λ3-iodanes with tetrahydrofuran

Author keywords

Borane; Radical; Reduction; 3 iodane

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; BORANE DERIVATIVE; DIPHENYLIODONIUM SALT; TETRAHYDROFURAN;

EID: 0038200989     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01331-5     Document Type: Article
Times cited : (15)

References (33)
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    • note
    • 4. Yields of the products were analyzed by GC (FFS ULBON HR-1 capillary column, 0.25 mm×50 m).
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    • note
    • -1. See Ref. 8b.
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    • 1a
    • 1a.
  • 28
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    • note
    • When the reduction of 1a using 1.3 equiv. of tri(sec-butyl)borane was carried out in THF-cyclohexane (5:95), the ratio of the phenyl-iodine(III) to the vinyl-iodine(III) bond cleavage changed to 89:11.
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    • Partial negative charge developed is more effectively stabilized by a phenyl group than by a vinyl group, see:
    • Partial negative charge developed is more effectively stabilized by a phenyl group than by a vinyl group, see: Dessy R.E., Kitching W., Psarras T., Salinger R., Chen A., Chivers T. J. Am. Chem. Soc. 88:1966;460.
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    • Dessy, R.E.1    Kitching, W.2    Psarras, T.3    Salinger, R.4    Chen, A.5    Chivers, T.6


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