CeCl3/NaClO: a safe and efficient reagent for the allylic chlorination of terminal olefins

Moreno‐Dorado, F. Javier; Guerra, Francisco M.; Manzano, Francisco L.; Aladro, F. Javier; Jorge, Zacarías D.; Massanet, Guillermo M.

doi:10.1016/s0040-4039(03)01630-7

Cited by 43 publications

(38 citation statements)

References 14 publications

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“…[12][13][14][15][16] This investigation shows clearly the role of MoCl 5 /NaOCl system in the activation and orientation of the reaction toward the desired product.…”

Section: Resultsmentioning

confidence: 98%

“…[8][9][10][11] Chloride compounds can be prepared directly by bubbling molecular chlorine, but the difficulty of handling chlorine gas limits this procedure. 12 Other authors have shown a convenient method for this transformation using solid CO 2 and calcium hypochlorite 13,14 or a combination of Vilsmeier reagent and H 2 O 2 . 15 However, this procedure is limited to non acid-sensitive substrates.…”

Section: Introductionmentioning

confidence: 99%

“…15 CeCl 3 or InCl 3 combined with NaOCl have been reported as efficient systems for allylic chlorination of terminal olefins. [12][13][14][15][16] In line with our continuous interest in the functionalization of natural terpenic olefins, [5][6][7] we report here the result of our investigation on the allylic chlorination using a combination of sodium hypochlorite and molybdenum pentachloride.…”

Section: Introductionmentioning

confidence: 99%

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Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

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MoCl 5 é usado como eficiente agente na cloração alílica de olefinas terpênicas na presença de NaOCl como doador de cloro. Vários terpenóides são convertidos aos cloretos de alila correspondentes em moderados a bons rendimentos em condições reacionais brandas e otimizadas. Diferentes precursores de molibdênio são estudados. Dentre eles, MoO 3 fornece bom rendimento, mas depois de um tempo de reação maior.MoCl 5 is applied as efficient agent in allylic chlorination of terpenic olefins in the presence of NaOCl as chlorine donor. Various terpenes are converted to the corresponding allylic chlorides in moderate to good yield under mild and optimized reaction conditions. Different molybdenum precursors are also studied. Among them, MoO 3 gives good yield, but after a longer reaction time.

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“…[12][13][14][15][16] This investigation shows clearly the role of MoCl 5 /NaOCl system in the activation and orientation of the reaction toward the desired product.…”

Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Allylic chlorination of terpenic olefins using a combination of MoCl5 and NaOCl

Boualy¹,

Firdoussi²,

Ali³

et al. 2011

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…The whole process involved protection of isopentenyl alcohol, allylic chlorination, 14 arene-catalyzed lithiation 15 in the presence of a carbonyl compound, and deprotection. Instead, we decided to use isopentenyl alcohol (2) as the direct source of dianion 5 and study its reactivity with carbonyl compounds.…”

Section: Figurementioning

confidence: 99%

“…Compounds 10a and 10b did not require any further purification, while compounds 10c-f were purified by column chromatography (silica gel, hexane-EtOAc,). (2R*,3aR*,6aS*)-2-Butylhexahydrofuro[2,3-b]furan (10d 129 (31), 128 (16), 117 (11), 115 (16), 107 (21), 105 (21), 104 (22), 91 (21), 84 (100), 83 (19), 77 (22), 70 (22), 69 (14), 56 (15), 55 (20).…”

Section: -Ethyl-3-methyleneheptane-15-diol (9a)mentioning

confidence: 99%