96556-34-2Relevant academic research and scientific papers
Reductive cleavage of acetals and ketals with 9-borabicyclo[3.3.1]nonane
Soderquist, John A.,Kock, Iveliz,Estrella, Maria E.
, p. 1076 - 1079 (2012/12/23)
The reductive cleavage of benzaldehyde acetals and acetophenone ketals with the air-stable crystalline 9-borabicyclo[3.3.1]-nonane dimer provides monobenzylated ether derivatives of diols and 1,2-oxygen-transposed β-phenethyl alcohols, respectively. The boron moiety is effectively recovered through simple procedures which involve convenient air-stable reagents and boron byproducts. The process is particularly selective for 1,3-diols giving the more substituted monobenzyl ether derivatives exclusively. With acetophenone ketals both reduction and elimination occur, permitting 9-BBN-H to hydroborate the resulting styrene to produce 1,2-oxygen-transposed β-phenethyl alcohols cleanly. Potential applications of this new process were illustrated with the synthesis of the hallucinogen, mescaline, and the analgesic, ibufenac.
