Reaction of bromonaphthalene with potassium tert-butoxide and tert-butyl alcohol in dimethyl sulfoxide

Bradshaw, Jerald S.; Hales, Richard H.

doi:10.1021/jo00801a016

Cited by 13 publications

(10 citation statements)

References 5 publications

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“…In the case of 1-bromonaphthalene, it appears that very easy elimination to the corresponding benzyne occurred. Addition of tert -butoxide occurred selectively at the 2-position, ultimately affording 2- t- butoxynaphthalene 17 [ 22 ]. Even allowing for that, 1-naphthyl radicals were clearly also formed as shown by the formation of 6g and 15g .…”

Section: Resultsmentioning

confidence: 99%

Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide

2015

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Section: Resultsmentioning

confidence: 99%

Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide

2015

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“…lowing reactants: bromonaphthalene-potassium tertbutoxide-íerí-butyl alcohol-DMSO. 5 The mole per cent ratio of 1-substituted products to 2-substituted products was found to be 0.36 ± 0.02 under all conditions except when the initial concentration of base was greatly reduced or when the initial concentration of alcohol was eliminated. The fact that this ratio was obtained with both 1-and 2-bromonaphthalene indicated that 1,2-dehydronaphthalene was an intermediate in that reaction.…”

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confidence: 84%

“…The fact that this ratio was obtained with both 1-and 2-bromonaphthalene indicated that 1,2-dehydronaphthalene was an intermediate in that reaction. 5 We now report on the reaction of 1-and 2-iodo-, -chloro-, and -fluoronaphthalenes with potassium íeríbutoxide in a ieri-butyl alcohol-DMSO solvent mixture and compare the results found with those of the bromonaphthalene reaction. 5 The iodoand chloronaphthalene reactions were found to be very similar to the bromonaphthalene reactions.…”

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confidence: 95%

“…5 We now report on the reaction of 1-and 2-iodo-, -chloro-, and -fluoronaphthalenes with potassium íeríbutoxide in a ieri-butyl alcohol-DMSO solvent mixture and compare the results found with those of the bromonaphthalene reaction. 5 The iodoand chloronaphthalene reactions were found to be very similar to the bromonaphthalene reactions. However, the fluoronaphthalene reactions were found to proceed by way of direct nucleophilic substitution rather than the aryne mechanism.…”

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Reaction of monohalonaphthalenes with potassium tert-butoxide and tert-butyl alcohol in dimethyl sulfoxide

Bradshaw¹,

Hales²,

Pratt³

1971

J. Org. Chem.

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“…Chem., 28, 887 (1963). (4) In principle, the C-10 methyl group of d-camphor could be labeled and then transformed into the C-8 methyl group of Z-camphor by racemization and resolution,5 but this procedure promised to be more tedious than the one adopted and would have given at most 50% yield per cycle.…”

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Reaction of the bromo- and fluoronaphthalenes with butyl mercaptide in dimethyl sulfoxide

Bradshaw¹,

South²,

Hales³

1972

J. Org. Chem.

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Fluoro-and 1-bromonaphthalenes reacted with «-butyl mercaptide in DMSO to give «-butyl 1-naphthyl sulfide in good yields. 2-Fluoroand 2-bromonaphthalenes reacted in a similar manner to yield «-butyl 2naphthyl sulfide. ieri-Butyl mercaptide reacted with the fluoroand bromonaphthalenes to give the corresponding ieri-butyl naphthyl sulfides. These reactions proved to be direct aromatic nucleophilic substitution reactions.In a continuation of our interest in the base-catalyzed reactions of the halonaphthalenes,3•4 we have treated the bromoand fluoronaphthalenes with n-butyl and ferf-butyl mercaptides in dimethyl sulfoxide (DMSO).The products of these reactions were the corresponding alkyl naphthyl sulfides.Although there is much knowledge concerning the reactions of thiophenoxide and thiocyanate with aromatic halogen compounds5-7 very little work has been done with the alkyl mercaptides. Miller has reported that methyl mercaptide is a much stronger nucleophile in aromatic nucleophilic substitution than thiophenoxide.8'9 Caubere and coworkers have studied the reactions of ethyl mercaptide with bromoand fluorobenzene in hexamethylphosphotriamide (H-MPT).10'11 Results and DiscussionA mixture of the halonaphthalene, butanethiol, sodium methoxide, and DMSO was heated at reflux for 1 hr. Sodium methoxide was used as the base since the thiol is a much stronger acid than methanol.12 Thus the solution would contain methanol and sodium butyl mercaptide. The completed mixture was added to water. The neutral fraction was separated and the products were analyzed by vapor phase chromatography (vpc).The products proved to be the appropriate alkyl naphthyl sulfide and the dibutyl disulfide. For example, w-butyl 2-naphthyl sulfide was obtained in the reaction using n-butyl mercaptide and 2-bromoor 2-fluoronaphthalene. No methyl naphthyl ether was observed in any of these reactions. Also no evidence of the 1,2-dehydronaphthalene intermediate, previously observed,3'4 was detected. This was shown by the fact that no 2-napththyl sulfide was isolated from 1bromoor l-fluoronaphthalene.

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Reaction of bromonaphthalene with potassium tert-butoxide and tert-butyl alcohol in dimethyl sulfoxide

Cited by 13 publications

References 5 publications

Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide

Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide

Reaction of monohalonaphthalenes with potassium tert-butoxide and tert-butyl alcohol in dimethyl sulfoxide

Reaction of the bromo- and fluoronaphthalenes with butyl mercaptide in dimethyl sulfoxide

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