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University of Pittsburgh
Organic chemists continually search for transformations to produce compounds in increasingly efficient and expedient ways, and to synthesize new compounds possessing interesting properties. One particularly appealing strategy is to exploit underutilized functional groups. By using this strategy, novel arrays of atoms that were previously unattainable are made possible. There are hurdles to overcome with this approach, that include, but are not limited to, an incomplete understanding of functional group compatibility issues that may arise during their preparation or caused by their presence in subsequent reactions. Even after decades of use, allenes can still be classified as an underutilized functional group. However, great advances in the chemistry of allenes have been made since the 1970s when they were regarded as difficult to prepare and very reactive, and not commonly encountered.
Focusing on a particular functional group at first glance may seem trivial and obvious, but the importance of these types of studies is underscored by the fact that numerous Nobel prizes have been awarded for the study “alkenes in synthesis”. More importantly, transformations involving allenes can provide new scaffolds that lead to an expansion of chemical space where currently nearly half of all existing organic compounds can be described by a mere 143 molecular frameworks. This data supports the notion that we tend towards compounds and functionalities with which we are familiar and understand, but this, nevertheless, creates a limitation to our knowledge of our field.
This Thematic Series represents contributions from leading chemists exploring a wide range of reactions involving allenes as reactants or products. The articles within detail discoveries surrounding the allene group and provide knowledge that chemists need in order to make informed decisions about whether or not to include an allene in a synthetic plan.
Kay M. Brummond
Beilstein J. Org. Chem. 2011, 7, 394–395. published 07 Apr 2011Editorial
CuCl-catalyzed aerobic oxidation of 2,3-allenols to 1,2-allenic ketones with 1:1 combination of phenanthroline and bipyridine as ligands
Shuxu Gao, Yu Liu, Shengming Ma
Beilstein J. Org. Chem. 2011, 7, 396–403. published 07 Apr 2011Full Research Paper
Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.01,5]dodecenone
Fuyuhiko Inagaki, Naoya Itoh, Yujiro Hayashi, Yumi Matsui, Chisato Mukai
Beilstein J. Org. Chem. 2011, 7, 404–409. published 07 Apr 2011Full Research Paper
An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts
Ryuji Hayashi, John B. Feltenberger, Andrew G. Lohse, Mary C. Walton, Richard P. Hsung
Beilstein J. Org. Chem. 2011, 7, 410–420. published 07 Apr 2011Full Research Paper
Synthesis of 5-(2-methoxy-1-naphthyl)- and 5-[2-(methoxymethyl)-1-naphthyl]-11H-benzo[b]fluorene as 2,2'-disubstituted 1,1'-binaphthyls via benzannulated enyne–allenes
Yu-Hsuan Wang, Joshua F. Bailey, Jeffrey L. Petersen, Kung K. Wang
Beilstein J. Org. Chem. 2011, 7, 496–502. published 19 Apr 2011Full Research Paper
Tomoya Miura, Tsuneaki Biyajima, Takeharu Toyoshima, Masahiro Murakami
Beilstein J. Org. Chem. 2011, 7, 578–581. published 09 May 2011Full Research Paper
Gold-catalyzed regioselective oxidation of terminal allenes: formation of α-methanesulfonyloxy methyl ketones
Yingdong Luo, Guozhu Zhang, Erik S. Hwang, Thomas A. Wilcoxon, Liming Zhang
Beilstein J. Org. Chem. 2011, 7, 596–600. published 11 May 2011Full Research Paper
Complete transfer of chirality in an intramolecular, thermal [2 + 2] cycloaddition of allene-ynes to form non-racemic spirooxindoles
Kay M. Brummond, Joshua M. Osbourn
Beilstein J. Org. Chem. 2011, 7, 601–605. published 12 May 2011Letter
Peter Wipf, Marija D. Manojlovic
Beilstein J. Org. Chem. 2011, 7, 824–830. published 17 Jun 2011Full Research Paper
Da Xu, Michael A. Drahl, Lawrence J. Williams
Beilstein J. Org. Chem. 2011, 7, 937–943. published 05 Jul 2011Letter