156480-40-9Relevant academic research and scientific papers
A One-step and Chemoselective Conversion of Silyl-protected Alcohols into the Corresponding Acetates
Oriyama, Takeshi,Oda, Mihoko,Gono, Junko,Koga, Gen
, p. 2027 - 2030 (1994)
A reagent system of acetyl bromide combined with a catalytic amount of tin(II) bromide cleaves readily trialkylsilyl ethers to give the corresponding acetates in high yields under very mild conditions.
A facile and efficient one-step conversion of alcohol triphenylmethyl ethers to the corresponding acetates
Kobayashi, Kumiko,Watahiki, Tsutomu,Oriyama, Takeshi
, p. 484 - 486 (2007/10/03)
Alcohol triphenylmethyl (trityl) ethers were readily and efficiently transformed into the corresponding acetates by reaction with acetyl bromide. Triphenylmethyl ethers can also be transformed into the corresponding substituted acetates in high yields by the use of various substituted acetyl chlorides combined with sodium iodide.
ZrCl4 as a mild and efficient catalyst for the one-pot conversion of TBS and THP ethers to acetates
Reddy, Ch. Sanjeeva,Smitha,Chandrasekhar
, p. 4693 - 4695 (2007/10/03)
A mild, efficient and chemoselective method has been developed for the direct transformation of tert-butyldimethylsilyl and tetrahydropyranyl protected alcohols into the corresponding acetates with acetic anhydride and zirconium(IV) chloride as the catalyst in acetonitrile, in a one-pot reaction with high yields and short reaction times. This method has been applied to a variety of substrates.
Differentation between Carbonyls and Acetals in 1,3-Dithiane and 1,3-Dithiolane Synthesis Catalyzed by Organotin Triflates
Sato, Tsuneo,Otera, Junzo,Nozaki, Hitosi
, p. 4971 - 4978 (2007/10/02)
Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates.In these competition reactions, various types of carbonyls and acetals are differentiated.Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals.The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones.Conversely, an aromatic acetal is more reactive than its parent aldehyde.In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates.However, aromatic acetals react preferentially over aliphatic acetals.Ketones of different types are also differentiated.No such discrimination can be achieved by conventional methods.Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals.Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.
