| Identification | Back Directory | [Name]
9-Allyl-9-borabicyclo[3.3.1]nonane | [CAS]
53317-08-1 | [Synonyms]
9-Allyl-9-borabicyclo[3.3.1]nonane
B-Allyl-9-borabicyclo[3.3.1]nonane
9-Borabicyclo[3.3.1]nonane, 9-(2-propen-1-yl)- | [Molecular Formula]
C11H19B | [MDL Number]
MFCD16876437 | [MOL File]
53317-08-1.mol | [Molecular Weight]
162.08 |
| Hazard Information | Back Directory | [Uses]
9-Allyl-9-borabicyclo[3.3.1]nonane could be used as an allylating reagent for aldehydes, ketones, acid chlorides, amides, and acid anhydrides; reagent for diastereo- and enantioselective allylation of aldimines; diastereoselective allylation of acetals[1-9].
| [Synthesis]
The Preparative Method of 9-Allyl-9-borabicyclo[3.3.1]nonane: prepared from Allyl Bromide and B-methoxy-9-BBN according to a literature procedure. Crotyl-9-BBN and 2-methallyl-9-BBN are similarly prepared from the corresponding allylic bromides.
| [storage]
Handling, Storage, and Precautions: the neat liquid is highly flammable and must be stored in the absence of air and moisture. 9-Allyl-9-borabicyclo[3.3.1]nonane (Allyl-9-BBN) may be kept as a CH2Cl2 or THF solution under N2 atmosphere. Use in a fume hood.
| [References]
1. Kramer, G. W.; Brown, H. C. JOM 1977, 132, 9. 2. Kramer, G. W.; Brown, H. C. JOC 1977, 42, 2292. 3. Yamamoto, Y.; Komatsu, T.; Maruyama, K. JOM 1985, 285, 31. 4. Vara Prasad, J. V. N.; Rich, D. H. TL 1990, 31, 1803. 5. Yamamoto, Y.; Komatsu, T.; Maruyama, K. JACS 1984, 106, 5031. 6. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. JACS 1986, 108, 7778. 7. Yamamoto, Y.; Ito, W.; Maruyama, K. CC 1985, 1131. 8. Yamamoto, Y.; Komatsu, T.; Maruyama, K. CC 1985, 814. 9. Yamamoto, Y.; Nishii, S.; Yamada, J. JACS 1986, 108, 7116.
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