Molecular addition compounds. 14. Convenient preparations of representative dialkylborane reagents using the new, highly reactive N- ethyl-N-isopropylaniline-borane reagent (BACH-EI(TM))

Tetrahedron

Volumn 55, Issue 19, 1999, Pages 5991-6000

  Brown, Herbert C ^a   Kanth, Josyula V B ^a,b   Zaidlewicz, Marek ^b  

^a PURDUE UNIVERSITY   (United States)

^b NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

Amine boranes; Dialkylboranes; Hydroboration

Indexed keywords

ANILINE DERIVATIVE; BORANE DERIVATIVE; DIOXANE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; MOLECULAR STABILITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033532122     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00272-0     Document Type: Article

References (29)

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2. (b) Pelter, A.; Smith, K.; Brown, H. C.; Borane Reagents; Academic Press: London, 1988.
3. (c)Encyclopedia of Organic Synthesis, Paquette, L. Ed., J. Wiely, New York, 1995.
4. (a) Lane, C. F.; Aldrichemica Acta, 1973, 6, 51.
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12. Brown, H. C.; Kanth, J. V. B.; Zaidlewicz, M.; J. Org. Chem., 1998, 63, 5154.
13. (a) Brown, H. C.; Zaidlewicz, M.; Dalvi, P. V.; Narasimhan, S.; Mukhopadyay, A.; Organometallics, 1999, 18, in press.
14. (b) Brown, H. C.; Kanth, J. V. B.; Zaidlewicz, M.; Organometallics, 1999, 18, in press.
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17. All these partially substituted boranes exist mainly as diborane dimers, but the monomeric forms are shown for the sake of convenience.
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26. Previously we observed that monoglyme and diglyme are superior media for obtaining high yields and high purities of 9-BBN and similar crystalline dialkylboranes. See, Soderquist, J. A.; Brown, H. C.; J. Org. Chem., 1981, 46, 4599. The present study shows that dioxane likewise is especially favorable for the preparation and isolation of such crystalline dialkylboranes.
27. Sinclair, J. A.; Brown, H. C.; J. Org. Chem. 1976, 41, 1078.
28. D +51.6°: Johnson, W. S.; Frei, B.; Gopalan, A. S. J. Org. Chem. 1981, 46, 1512.
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