110-52-1Relevant articles and documents
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Marshall et al.
, p. 163,167 (1979)
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Goldsworthy
, p. 482,485 (1931)
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Syntheses of [13C,15N]-Labeled Polyamines
Hara, Takeshi,Xu, Yong Ji,Sasaki, Hitomi,Niitu, Masaru,Samejima, Keijiro
, p. 1005 - 1012 (2000)
[1,4-13C2, 1,4-15N2]butanediamine (1), a key compound in the syntheses of [5,8-13C2, 1,4,8-15N3]spermidine (2) and [5,8-13C2, 1,4,8,12-15N4]spermine (3), has been prepared as part of a 6-step process from 1,2-dibromoethane using potassium [13C]cyanide and potassium [15N]phthalimide. In the course of the syntheses, it was found that 1,4-dibromobutane was generated from tetrahydrofuran when bromination using triphenylphosphine and tetrabromomethane took place. A high-yield preparation of monobenzyloxycarbonyl (Z) derivative of 1, a precursor for 2, was obtained using a water-soluble Z reagent, Z-DSP, in a two-phase system of alkaline solution and chloroform. All the steps for 1, 2, and 3, were aimed at minimizing the loss of stable isotopes.
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Bunnett,Brotherton
, p. 834 (1957)
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Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes
Chen, Shuming,Gieuw, Matthew H.,Houk, K. N.,Ke, Zhihai,Yeung, Ying-Yeung
, p. 9426 - 9433 (2020/10/02)
Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3
1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction
Essiz, Sel?uk,Da?tan, Arif
, p. 150 - 156 (2019/05/16)
An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.
Mild one-step synthesis of dibromo compounds from cyclic ethers
Billing, Peter,Brinker, Udo H.
, p. 11227 - 11231 (2013/02/23)
A novel one-step method for mildly converting cyclic ethers into dibromo compounds is reported. Alcohols, oximes, aldehydes, and ketones are known to react under Appel or Corey-Fuchs reaction conditions, but apparently these have never been applied to oxetanes or larger cyclic ethers. Treatment of 3,3-dimethyloxetane (1) with tetrabromomethane and triphenylphosphine gave the corresponding dibromo compound 1,3-dibromo-2,2-dimethylpropane (2). The less-strained homologue oxolane (6) was also reacted giving 1,4-dibromobutane (7) in a 93% yield. Mechanistic interpretations are offered to explain the observed reaction rates of the conversions described.