Dehydrogenation of polycyclic ketones using trichloromethyl cation in superacid

Martin, Amélie; Jouannetaud, Marie‐Paule; Jacquesy, Jean‐Claude

doi:10.1016/0040-4039(96)01736-4

Cited by 6 publications

(2 citation statements)

References 8 publications

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“…Jacquesy and coworkers [ 24 ] have investigated the chemistry of polycyclic ketones in HF-SbF 5 -CCl 4 , a powerful reagent combination for dehydrogenation. For example, 2-decalone ( 51 ) (primarily trans ) was reacted with HF-SbF 5 -CCl 4 at 0 °C to give products 52 and 53 in 25% and 12% yields, respectively ( Scheme 12 ).…”

Section: Reviewmentioning

confidence: 99%

Molecular rearrangements of superelectrophiles

Klumpp¹

2011

Beilstein J. Org. Chem.

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SummarySuperelectrophiles are multiply charged cationic species (dications, trications, etc.) which are characterized by their reactions with weak nucleophiles. These reactive intermediates may also undergo a wide variety of rearrangement-type reactions. Superelectrophilic rearrangements are often driven by charge–charge repulsive effects, as these densely charged ions react so as to maximize the distances between charge centers. These rearrangements involve reaction steps similar to monocationic rearrangements, such as alkyl group shifts, Wagner–Meerwein shifts, hydride shifts, ring opening reactions, and other skeletal rearrangements. This review will describe these types of superelectrophilic reactions.

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Section: Reviewmentioning

confidence: 99%

Molecular rearrangements of superelectrophiles

Klumpp¹

2011

Beilstein J. Org. Chem.

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“…74 The dehydrogenation of steroidal ketones such as 19-norandrost-4-ene-3,17-dione with copper bromide has yielded 75 estrone derivatives. The trichloromethyl cation has also been described 76 as a dehydrogenating agent. The preparation of steroidal dioxolanes 34 by the fragmentation of peroxyhemiacetals has been reported.…”

Section: Carbonyl Compoundsmentioning

confidence: 99%