129454-53-1Relevant 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.
An aldol - Bislactonization route to α-methylene bis-γ-butyrolactones
Lertvorachon, Jittiwud,Meepowpan, Puttinan,Thebtaranonth, Yodhathai
, p. 14341 - 14358 (2007/10/03)
The syntheses of α-methylene γ-butyrolactones and α-methylene bis- γ-butyrolactones are made simple through the use of the versatile dimethyl itaconate - anthracene adduct, 1.
Dialkyl and diaryl boron halides: reductive opening of benzylidene acetals
Guindon, Yvan,Girard, Yves,Berthiaume, Sylvie,Gorys, Vida,Lemieux, Rene,Yoakim, Christiane
, p. 897 - 902 (2007/10/02)
Dimethylboron bromide or diphenylboron bromide can be used in combination with borane to achieve the regiocontrolled conversion of benzylidene acetals to their corresponding hydroxy benzyl ethers with moderate to high yields.
