Die Umlagerung des 9‐Cyan‐
            <i>cis</i>
            ‐bicyclo[6.1.0]nona‐2,4,6‐trien‐9‐yl‐Anions in das 9‐Cyanbicyclo[4.2.1] nona‐2,4,7‐trien‐9‐yl‐Anion Zur Frage der Bicycloaromatizität

Boche, Gernot; Martens, D.

doi:10.1002/cber.19791120117

Cited by 10 publications

References 33 publications

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Intermolecular Metal‐Catalyzed Carbenoid Cyclopropanations

2001

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The metal‐catalyzed decomposition of diazo compounds in the presence of alkenes is a well‐established reaction. Since the original Organic Reactions review on the reaction of ethyl diazoacetate with alkenes and aromatic compounds in 1970, several new developments have revolutionized this area of chemistry. Most notably, major advances have been made in catalyst design such that highly chemoselective, diastereoselective and enantioselective carbenoid transformations can now be achieved. Furthermore, it has been recognized that a wide array of carbenoid structures can be utilized in this chemistry, leading to a broad range of synthetic applications. This chapter comprises coverage of the metal‐catalyzed intermolecular cyclopropanations of diazo compounds containing at least one adjacent electron‐withdrawing group. The coverage of diazoacetate chemistry will be limited to material since 1970 because the previous Organic Reactions review covers the earlier literature. The alkene component is limited to alkenes, dienes, furans, and pyrroles because these are the systems that have resulted in the greatest developments since the 1970 review. Metal‐carbenoid intermediates derived from diazo compounds undergo a variety of useful reactions, including cyclopropanation, insertion, and ylide formation. In recent years several excellent reviews have appeared on various aspects of this chemistry. Three recent reviews have focused on asymmetric intermolecular cyclopropanations. Several books and reviews on carbenoid chemistry have major sections on intermolecular cyclopropanations. Because of the historical central prominence of carbenoids derived from diazoacetates, most reviews have tended to focus on this class of carbenoids. In this chapter, a comparison is presented of the chemical differences that exist among the major classes of carbenoids that contain adjacent electron‐withdrawing groups. The extensive nature of the topic precludes coverage of related reactions such as the metal‐catalyzed decomposition of diazoalkanes, phenyldiazoalkanes, or vinyldiazoalkanes that lack adjacent electron‐withdrawing functionality. Other cyclopropanation reactions such as the Simmons‐Smith reaction, photochemical or thermal decomposition of diazo compounds in the presence of alkenes, and cyclopropanation using stoichiometric metal carbenes are not covered.

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Intermolecular Metal‐Catalyzed Carbenoid Cyclopropanations

2001

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Cyclopropyl radicals, anion radicals and anions

Boche

Walborsky²

1990

PATAI'S Chemistry of Functional Groups

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Zur Struktur der Lithiumverbindungen von Sulfonen, Sulfoximiden, Sulfoxiden, Thioethern und 1,3‐Dithianen, Nitrilen, Nitroverbindungen und Hydrazonen

Boche

1989

Angewandte Chemie

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170

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Acceptor-substituierte Lithiumverbindungen LiA-CR'R', bei denen der Acceptor A eine RC(0)-, N=C-, RS02-, RS(0)NR-, RSO-, RS-, 0 2 N -oder RC(N-NR,)-Gruppe sein kann, spielen in der organischen Synthese seit langem eine gro13e Rolle. Ihre Bedeutung ist in den letzten fiinfzehn Jahren nochmals gestiegen, nachdem man in zunehmendem Ma13 gelernt hatte, sie in chemo-, regio-, diastereo-und enantioselektiven Reaktionen einzusetzen. Dabei ist bemerkenswert, dal3 man iiber die Strukturen von solchen Verbindungen, wenn iiberhaupt etwas, meist nur wenig wul3te. Es wundert daher nicht, dal3 das Interesse daran in jungster Zeit stark zugenornmen hat. Im folgenden werden die neueren Untersuchungen zur Struktur der Lithiumverbindungen von Sulfonen, Sulfoximiden, Sulfoxiden, Thioethern und 1,3-Dithianen, Nitrilen, Nitroverbindungen und Hydrazonen zusammengefal3t. Die Festkorperstrukturuntersuchungen der letzten Jahre stehen dabei im Mittelpunkt. Sie werden erganzt durch Untersuchungen in Losung und durch Strukturberechnungen. Wo es moglich ist, wird auf strukturelle Verwandtschaften und Unterschiede zwischen den einzelnen Aggregatzustanden und auf den Zusammenhang zwischen Struktur und Reaktivitat hingewiesen.

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Die Umlagerung des 9‐Cyan‐ cis ‐bicyclo[6.1.0]nona‐2,4,6‐trien‐9‐yl‐Anions in das 9‐Cyanbicyclo[4.2.1] nona‐2,4,7‐trien‐9‐yl‐Anion Zur Frage der Bicycloaromatizität

Abstract: Nachdem es sich gezeigt hatte, da13 die bicyclische Lithiumverbindung 1 a keinezwischenstufe bei der Bildung der [9]Annulen-Anionen 2 bzw. 3 darstellt ') ~ nur Lithiocyclo-

Cited by 10 publications

References 33 publications

Intermolecular Metal‐Catalyzed Carbenoid Cyclopropanations

Intermolecular Metal‐Catalyzed Carbenoid Cyclopropanations

Cyclopropyl radicals, anion radicals and anions

Zur Struktur der Lithiumverbindungen von Sulfonen, Sulfoximiden, Sulfoxiden, Thioethern und 1,3‐Dithianen, Nitrilen, Nitroverbindungen und Hydrazonen

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