Konfigurations- und konformationsisomere paratrope, rotationsdynamische Tetraepoxy[32]annulene(6.2.6.2) und diatrope Tetraoxa[30]porphyrin(6.2.6.2)-Dikationen: Nachweis eines Tetraepoxy[31]annulen(6.2.6.2)-Radikalkations

Märkl, Gottfried; Ehrl, Robert; Sauer, Heinrich; Kreitmeier, Peter; Burgemeister, Thomas

doi:10.1002/(sici)1522-2675(19990113)82:1<59::aid-hlca59>3.0.co;2-8

Cited by 18 publications

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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The McMurry coupling reaction has been recognized as one of the most efficient methods for the synthesis of alkenes from carbonyl compounds. This reaction can be applied to the preparation of various alkenes that are otherwise difficult to prepare. For example, sterically congested tetrasubstituted alkenes as well as medium to large membered rings involving natural products may be accessed via this process. This coupling utilizes various low‐valent titanium reagents generated by the reduction of titanium (III or IV) chloride with K, Zn, LiAlH 4 , C 8 K, amongst others. Furthermore, a variety of low‐valent metal species other than titanium, including aluminum, zirconium, niobium, molybdenum, indium, tungsten, and samarium, have also been found to promote the reductive coupling of carbonyl compounds. The scope and limitations of these reagent systems are reviewed in this chapter, together with the stereochemistry and reaction mechanism. This reaction is categorized into four coupling modes: i) homocoupling giving symmetrical alkenes, ii) mixed coupling giving unsymmetrical alkenes, iii) intramolecular coupling giving cycloalkenes, and iv) tandem coupling giving cyclic polyenes. Characteristics of these reaction modes are described briefly. A selection of synthetic applications are reviewed, including examples of the preparation of sterically congested and strained alkenes, medium to large‐ring compounds, biologically active targets, as well as substrates applicable in material science. Experimental conditions used for this versatile process are summarized to assist the choice of suitable conditions.

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The McMurry Coupling and Related Reactions

Takeda

Tsubouchi

2013

Organic Reactions

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1,6-Dibromohexa-1,3,5-triene − Stereocontrolled Synthesis of Monosubstituted and Disubstituted Hexatrienes by Palladium-Catalysed Cross-Coupling Reactions

et al. 2001

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1,6‐Dibromohexa‐1,3,5‐triene, previously described by us and easily obtained from 5‐bromopenta‐2,4‐dienal by condensation with bromomethylene triphenylphosphorane, is a versatile precursor for the synthesis of conjugated 1,3,5‐trienic derivatives of controlled configuration. In this paper, we describe the stereocontrolled synthesis of E,E,Z, E,E,E and Z,E,Z isomers of α‐bromo‐ω‐substituted‐1,3,5‐hexatrienes and 1,6‐disubstituted‐1,3,5‐hexatrienes. The synthesis is based on palladium‐catalysed single or double cross‐coupling reactions between the three isomers − 1E,3E,5Z, 1E,3E,5E and 1Z,3E,5Z − of the intermediate 1,6‐dibromohexa‐1,3,5‐triene and various organozinc reagents.

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