Studies on the Friedel Crafts Acylation of hydrindane

Davison, Gordon R.; Howard, Judith A. K.; Pitchford, N. A.; Jones, Alan M.; Rasburn, J. W.; Simpson, A. J.

doi:10.1016/s0040-4020(01)80208-8

Cited by 3 publications

(1 citation statement)

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“…This transformation can be considered to be an aliphatic Friedel–Crafts acylation, which is not without precedent: such reactions have been reported for other simple, unfunctionalized alkanes . (It should be noted that Friedel–Crafts acylations of several alkenes are also known …”

Section: Introductionmentioning

confidence: 96%

C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

et al. 2014

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Decalin undergoes reaction with aluminum trichloride and acetyl chloride to form a tricyclic enol ether in good yield, as first reported by Baddeley. This eye-catching transformation, which may be considered to be an aliphatic Friedel-Crafts reaction, has not previously been studied mechanistically. Here we report experimental and computational studies to elucidate the mechanism of this reaction. We give supporting evidence for the proposition that, in the absence of unsaturation, an acylium ion acts as a hydride acceptor, forming a tertiary carbocation. Loss of a proton introduces an alkene, which reacts with a further acylium ion. A concerted 1,2-hydride shift/oxonium formation, followed by elimination, leads to formation of the observed product.

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Section: Introductionmentioning

confidence: 96%

C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

et al. 2014

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ChemInform Abstract: Studies on the Friedel Crafts Acylation of Hydrindan.

et al. 1994

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Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

et al. 2013

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The functionalisation of decalin by means of an "aliphatic Friedel-Crafts" reaction was reported over fifty years ago by Baddeley et al. This protocol is of current relevance in the context of C-H activation and here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation of the products is described and a mechanistic rationale for their formation is presented. The "aliphatic Friedel-Crafts" procedure allows for production of novel oxygenated building blocks from abundant hydrocarbons and as such can be considered to add significant synthetic value in a single step.

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Studies on the Friedel Crafts Acylation of hydrindane

Cited by 3 publications

References 14 publications

C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

ChemInform Abstract: Studies on the Friedel Crafts Acylation of Hydrindan.

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

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Studies on the Friedel Crafts Acylation of hydrindane

Cited by 3 publications

References 14 publications

C–H Functionalization of sp3 Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

C–H Functionalization of sp3 Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

ChemInform Abstract: Studies on the Friedel Crafts Acylation of Hydrindan.

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

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Product

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C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

C–H Functionalization of sp³ Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin