Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Thomas, Allen A.; Monk, Keith A.; Abraham, Sonia; Lee, Stella; Garner, Charles M.

doi:10.1016/s0040-4039(01)00089-2

Cited by 12 publications

(4 citation statements)

References 10 publications

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“…Treatment of (+)-methylene camphor with NBS in the presence of pyridine resulted in a rapid rearrangement to yield a brominated (+)-methylenefenchone in high yield and purity (>96%) (Scheme 676). 1882 A combination of NBS and dibenzoyl peroxide or azobis(isobutyronitrile) was used to carry out the isomerization of (Z)-alkenes to the corresponding (E)-alkenes. 1883 The reaction was carried out by heating the allkene with 1.1 equiv of NBS in the presence of AIBN in CCl 4 at reflux temperature for 1 h (Scheme 677).…”

Section: Rearrangement Reactions Using Nbsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Rearrangement Reactions Using Nbsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…Freshly crystallized N-bromosuccinimide [22] (1.8 mmol, 315.0 mg) was added portionwise under argon to a solution of methyl (triphenylphosphoranylidene)acetate (1.6 mmol, 538.0 mg) in dry chloroform (5 mL) cooled to -20°C. The solution was stirred for 40 min at -20°C and then the solvent was evaporated under reduced pressure in a water bath at room temperature.…”

Section: Experimental Section General Procedures For the One-pot Synthmentioning

confidence: 99%

A Simple Synthesis of Functionalized 3‐Bromocoumarins by a One‐Pot Three‐Component Reaction

et al. 2010

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Functionalized 3‐bromocoumarins 2 have been prepared by a simple one‐pot bromination/Wittig/cyclization tandem process from methyl (triphenylphosphoranylidene)acetate, N‐bromosuccinimide and a series of 2‐hydroxybenzaldehydes. Owing to the commercial availability of salicylaldehyde derivatives, this approach offers such a diverse range of compounds that it fulfills the recent demand for the generation of large combinatorial chemical libraries based on the coumarin scaffold.

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“…Electrophilic bromination is the very important approach in the preparation of bromofunctionalized terpenoid derivatives, which are common as intermediates in organic synthesis because of the ease of further modifications via nucleophilic substitutions or various skeletal rearrangements and cyclizations [26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

Recyclization reactions of 8,10-dibromocamphor with Grignard and organolithium compounds

Verenka

Gorichko

2021

Fr. Ukr. J. Chem.

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Grignard reagents and organolithium compounds react with 8,10-dibromocamphor to afford substituted 1-methyl-2-methylenebicyclo[3.2.0]heptanes. Recyclization proceeds via intramolecular enolate alkylation and Grob fragmentation of the reaction intermediates. All compounds have been characterized by 1H, 13C and 19F NMR spectroscopy and their chemical composition proved by HRMS analyses. The relative spatial arrangement of substituents in the molecule of (1-methyl-2-methylenebicyclo[3.2.0]heptan-6-yl)diphenylmethanol was studied by NOESY experiments.

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Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Cited by 12 publications

References 10 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A Simple Synthesis of Functionalized 3‐Bromocoumarins by a One‐Pot Three‐Component Reaction

Recyclization reactions of 8,10-dibromocamphor with Grignard and organolithium compounds

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