83249-09-6Relevant academic research and scientific papers
Redox-Active Esters in Fe-Catalyzed C-C Coupling
Toriyama, Fumihiko,Cornella, Josep,Wimmer, Laurin,Chen, Tie-Gen,Dixon, Darryl D.,Creech, Gardner,Baran, Phil S.
, p. 11132 - 11135 (2016)
Cross-couplings of alkyl halides and organometallic species based on single electron transfer using Ni and Fe catalyst systems have been studied extensively, and separately, for decades. Here we demonstrate the first couplings of redox-active esters (both isolated and derived in situ from carboxylic acids) with organozinc and organomagnesium species using an Fe-based catalyst system originally developed for alkyl halides. This work is placed in context by showing a direct comparison with a Ni catalyst for >40 examples spanning a range of primary, secondary, and tertiary substrates. This new C-C coupling is scalable and sustainable, and it exhibits a number of clear advantages in several cases over its Ni-based counterpart.
3-Aminobicyclo[1.1.1]pentane-1-carboxylic Acid Derivatives: Synthesis and Incorporation into Peptides
Paetzel, Michael,Sanktjohanser, Maximilian,Doss, Alexander,Henklein, Peter,Szeimies, Guenter
, p. 493 - 498 (2007/10/03)
We have developed an efficient synthesis of derivatives of 3-aminobicyclo[1.1.1]pentane-1-carboxylic acid (7, 8, 9, and 10) starting from [1.1.1]propellane (3). These rigid analogues of γ-aminobutyric acid have been incorporated into linear and cyclic peptides using solution chemistry and solid-phase techniques. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Formation and reactions of bicyclo[1.1.1]pentyl-1 cations
Wiberg, Kenneth B.,McMurdie, Neil
, p. 11990 - 11998 (2007/10/03)
The ionization of 1-bicyclo[1.1.1]pentyl halides was shown to initially form the 1,3-bridged bicyclo[1.1.1]pentyl-l cation. It appears to be a transition state that leads to the bicyclo[1.1.0]butyl-1-carbinyl cation which can be trapped with azide ion and
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.
Toward a molecular-size "Tinkertoy" construction set. Preparation of terminally functionalized [n]staffanes from [1.1.1]propellane
Kaszynski, Piotr,Friedli, Andrienne C.,Michl, Josef
, p. 601 - 620 (2007/10/02)
A facile but low-yield synthesis of [n]staffanes (the oligomers of [1.1.1.]propellane 1, n =1-5) functionalized on one or both ends is described, and their properties are summarized. The substituents are -COOCH3, -n-C4H9, -C6H5, -Br, -I, and -SCOCH3, and their conversion to others, such as -COOH, -COCH3 and -SH, is demonstrated. It is proposed that these rod-shaped molecules will be useful in the development of a molecular-size civil engineering construction set analogous to children's toy construction sets.
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
Vibrational Spectrum, Structure, and Energy of Propellane
Wiberg, Kenneth B.,Dailey, William P.,Walker, Frederick H.,Waddell, Sherman T.,Crocker, Louis S.,Newton, Marshall
, p. 7247 - 7257 (2007/10/02)
The structure of propellane (bond lenghts and angles) was determined from an analysis of the rotational components of the infrared bands of the parent compound and of its d6 derivative, and it was found to be in good agreement with the structure ca
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.
