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Allene chemistry


Editor: Prof. Kay M. Brummond
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.



 
Overview

Allene chemistry

Kay M. Brummond

Beilstein J. Org. Chem. 2011, 7, 394–395. published 07 Apr 2011

Editorial

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 2011

Full 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 2011

Full 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 2011

Full 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 2011

Full Research Paper

Synthesis of cross-conjugated trienes by rhodium-catalyzed dimerization of monosubstituted allenes

Tomoya Miura, Tsuneaki Biyajima, Takeharu Toyoshima, Masahiro Murakami

Beilstein J. Org. Chem. 2011, 7, 578–581. published 09 May 2011

Full 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 2011

Full 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 2011

Letter

Homoallylic amines by reductive inter- and intramolecular coupling of allenes and nitriles

Peter Wipf, Marija D. Manojlovic

Beilstein J. Org. Chem. 2011, 7, 824–830. published 17 Jun 2011

Full Research Paper

Toward an integrated route to the vernonia allenes and related sesquiterpenoids

Da Xu, Michael A. Drahl, Lawrence J. Williams

Beilstein J. Org. Chem. 2011, 7, 937–943. published 05 Jul 2011

Letter