Ueber isomere Dehydrocamphersäuren, Lauronolsäuren und Bihydrolauro‐Lactone

Bredt, J.; Houben, J.-O.-S.; Levy, Paul

doi:10.1002/cber.19020350215

Cited by 68 publications

(30 citation statements)

References 3 publications

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“…From the 19th century on, the synthesis of molecules that deviated from the norm took a special place in the imagination of chemists. There are many examples to point to, molecules that violate Bredts rule [17] or the classical double-bond rule, or organometallic complexes in which the CO ligand bonds to a transition metal through its oxygen atom. Once theoreticians could contribute more or less reliably, they took to this game with a vengeance-one of the authors strategy for stabilizing squareplanar carbon is a good example: a veritable menagerie of (largely) hypothetical molecules was generated.…”

Section: Reasons For Making Molecules In Distressmentioning

confidence: 99%

Learning from Molecules in Distress

Hoffmann

Hopf

2008

Angew Chem Int Ed

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Going to extremes: Deformed molecules with “planar” carbon atoms, orthogonal double bonds, nonlinear triple bonds, and aromatic rings distorted into a boat structure have interested chemists for decades. This essay traces the reasons for this fascination, and finds them in the psyche of the researcher: the wish to transgress the limits of normalcy, the insatiable curiosity to extend the limits of method and mind, and the eternal human joy to find something new while playing.

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Section: Reasons For Making Molecules In Distressmentioning

confidence: 99%

Learning from Molecules in Distress

Hoffmann

Hopf

2008

Angew Chem Int Ed

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“…(a)The tricyclopropylmethyl cation was the first cyclopropylmethyl cation to be observed by NMR spectroscopy(52). (b) Bredt's rule(53) in its original form seems to exclude the possibility of formation of positive carbenium ion centers at bridgehead positions. Indeed, bridgehead halides proved to be extremely unreactive under solvolytic conditions.…”

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confidence: 99%

Superacids

Oláh

Prakash²,

Sommer³

1979

Science

291

196

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Superacids, although first referred to as early as 1927, were only extensively studied in the last decade. Acidities up to 10(12) times that of sulfuric acid have now been obtained. The extremely low nucleophilicity of the counterions in superacidic systems is especially useful for the preparation of stable, electron-deficient cations, particularly carbocations. Many of these cations, which were formerly detectable only in the gas phase, can now be studied in solution. Novel organic syntheses that are not possible in ordinary acidic media can also be achieved in superacids, including syntheses of economically important hydrocarbons. The unique ability of superacids to bring about hydrocarbon transformations, even to activate methane to undergo electrophilic oligocondensation, can open up new fields in chemistry.

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“…Den Widerstand gegen die Bildung von (4) und verwandten Bicyclen fchrte Bredt zutreffend auf die Ringspannung zuruck, die sich [**I Der altertiimelnde, aber noch iibliche Terminus ,,Bredtsche Regel" wird hier durch .. Bredt-Regel" ersetzt, der Als interessant und zukunftstrachtig erwies sich ein anderer G e~i c h t s p u n k t~~,~~ : Verhindert die Ringspannung die Ausbildung einer Doppelbindung am Bruckenkopf der Bicyclen (I) und (2), so gilt dies sicher auch fur niedergliedrige Verbindungen, etwa fur das Bicyclo[2.1 .I]hexanSystem -es gilt aber nicht uneingeschriinkt fur die hoheren Homologen von ( I ) und (2). denn bei hinreichend groDer Ringgliederzahl lassen sich Bruckenkopfolefine am Molekulmodell durchaus spannungsfrei konstruieren.…”

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Bredt‐Verbindungen und Bredt‐Regel

Köbrich¹

1973

Angewandte Chemie

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Herrn Professor Theodor Wieland zum 60. Gehurtstag gewidmetDie Bredt-Regel[*'', in fruheren Dezennien vor allem als aussonderndes Kriterium bei Strukturzuordnungen bewahrt, wurde in den vergangenen Jahren zum Stimulans fur Bemuhungen um die Synthese gespannter bicyclischer Systeme mit einer Bruckenkopfdoppelbindung. Auf der Grundlage der in solchen Systemen wirksamen Ringspannungskrafte wird eine erweiterte Bredt-Regel diskutiert. Die von dieser Regel betroffenen ,,Bredt-Verbindungen", zu denen auch bicyclische Systeme gehoren, die bisher nicht unter diesem Aspekt gesehen wurden (z. B. uberbruckte Methylen-cyclopropane), bilden ein klar umrissenes, interessantes Feld innerhalb der Chemie hochgespannter cyclisch-ungesattigter Kohlenwasserstoffe.

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Ueber isomere Dehydrocamphersäuren, Lauronolsäuren und Bihydrolauro‐Lactone

Cited by 68 publications

References 3 publications

Learning from Molecules in Distress

Learning from Molecules in Distress

Superacids

Bredt‐Verbindungen und Bredt‐Regel

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