83249-14-3Relevant academic research and scientific papers
Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents
Kanazawa, Junichiro,Koyamada, Kenta,Miyamoto, Kazunori,Uchiyama, Masanobu,Watanabe, Ayumi
supporting information, p. 1328 - 1334 (2020/08/14)
Sterically hindered three-dimensional (3D) alkyl halides are promising precursors for various reactions; however, they are difficult to synthesize via conventional reactions. We present an efficient and practical method for decarboxylative bromination of sterically hindered 3D aliphatic carboxylic acids using commercially available (diacetoxyiodo)benzene and potassium bromide, one of the most stable and cheapest bromine sources in nature. The present method features a metal-free/Br2-free system, mild reaction conditions, one-pot operation under air at room temperature, wide functional group compatibility, and gram-scale synthetic capability. This highly efficient reaction cleanly converts a broad range of carboxylic acids, the most inexpensive and readily available sources of highly strained/naturally occurring/drug-related scaffolds, into the corresponding alkyl bromides in good to high yields.
Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclopentanes
Della, Ernest W.,Taylor, Dennis K.
, p. 2986 - 2996 (2007/10/02)
The synthesis of a wide variety of 1,3-disubstituted bicyclopentanes is described, with particular emphasis on the generation of a series of 3-X-substituted bicyclopentyl bromides required for solvolytic studies.Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes; in some instances, transformations were effected via carbanionic-type intermediates.
Synthesis of Doubly Bridgehead Substituted Bicyclopentanes. Radical Transformations of Bridgehead Halides and Carboxylic Acids
Kaszynski, Piotr,Murdie, Neil D. Mc,Michl, Josef
, p. 307 - 316 (2007/10/02)
Synthetic transformations of the 1-bicyclopentyl bridgehead radicals 11 generated from the corresponding bridgehead iodides 3 and carboxilic acids 5 are described.The relatively high nucleophilicity of these radicals was utilized in reactions with
Polar Substituent Effects in 1,3-Disubstituted Bicyclopentanes
Applequist, Douglas E.,Renken, Terry L.,Wheeler, James W.
, p. 4985 - 4995 (2007/10/02)
The pKa's of eight 3-substituted bicyclopentanecarboxylic acids have been measured and found to correlate well with ?I constants.The value of ρI (2.23 +/- 0.12) is large but not large enough to propose any special perturbation of normal field-inductive effects by the close proximity (about 1.88 Ae) of the bridgehead carbons.Also determined were the products and rates of solvolyses of the p-nitrobenzoates of three 3-substituted 1-pentanes.The products were primarily unrearranged, and the rates again showed no surprisingsubstituent effects.A practical synthesis of 1,3-disubstituted bicyclopentanes has been developed and is described.
