B-Allyl-9-borabicyclo[3.3.1]nonane

Yoshinori Yamamoto

Yoshinori Yamamoto

Tohoku University, Japan

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Daniel Grant

Daniel Grant

Burnham Institute for Medical Research, La Jolla, CA, USA

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First published: 15 March 2009

Abstract

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[53317-08-1] C11H19B (MW 162.07)

InChI = 1S/C11H19B/c1-2-9-12-10-5-3-6-11(12)8-4-7-10/h2,10-11H,1,3-9H2/t10-,11-

InChIKey = VWDZBSSQLJNTMJ-XYPYZODXSA-N

(allylating reagent for aldehydes, ketones, acid chlorides, amides, and acid anhydrides;2 reagent for diastereo- and enantioselective allylation of aldimines;6, 8 diastereoselective allylation of acetals9)

Alternate Name: allyl-9-BBN.

Physical Data: bp 41.5–42 °C/0.05 mmHg.

Solubility: sol most organic solvents.

Preparative Methods: prepared from Allyl Bromide and B-methoxy-9-BBN according to a literature procedure.1 Crotyl-9-BBN and 2-methallyl-9-BBN are similarly prepared from the corresponding allylic bromides.

Handling, Storage, and Precautions: the neat liquid is highly flammable and must be stored in the absence of air and moisture. Allyl-9-BBN may be kept as a CH2Cl2 or THF solution under N2 atmosphere.2 Use in a fume hood.

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