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Volumn 61, Issue 6, 1996, Pages 2006-2012

A mechanistic approach to the reaction of 2,6-di-tert-butylphenol with an iodinating agent in methanol: Electrophilically assisted solvolysis of intermediary 4-iodocyclohexa-2,5-dienones

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONES; BIPHENOL; BUTYLPHENOL; DIENONES; H NMR SPECTROSCOPY; METHANOLYSIS; P-BENZOQUINONE; REACTION TIME;

EID: 0004376683     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951455n     Document Type: Article
Times cited : (27)

References (30)
  • 6
    • 76049126412 scopus 로고    scopus 로고
    • 2 (from Wako Chemicals) was determined by iodometric titration to be in fact 36%.
    • 2 (from Wako Chemicals) was determined by iodometric titration to be in fact 36%.
  • 7
    • 76049121851 scopus 로고    scopus 로고
    • 2O/MeOH.
    • 2O/MeOH.
  • 9
    • 76049115684 scopus 로고    scopus 로고
    • The substitution reaction of 12 with the other, minor nucleophiles, H2O and H2O2, can also be considered not shown in Scheme 2, 2,6-Di-tert-butylhydroquinone, the product expected from the hydrolysis of 12, was found in none of the reactions of 1 with I2/H2O2/ MeOH or I2/H2O/MeOH. The hydroquinone is presumed to have been readily oxidized to 6 under the reaction conditions. The product from the reaction between 12 and H2O2 is assumed to have also disintegrated into 6
    • 2 is assumed to have also disintegrated into 6.
  • 16
    • 76049114915 scopus 로고    scopus 로고
    • Attempted purification of the crude product of 13 obtained from the reaction of 14 has proved unsuccessful. The crude products of some other 4-hydro-4-alkoxy-2,6-di-tert-butylcyclohexa-2,5-dienones obtained by analogous means, however, have been successfully purified, and their structures have been unambiguously established. The results will be published elsewhere.
    • Attempted purification of the crude product of 13 obtained from the reaction of 14 has proved unsuccessful. The crude products of some other 4-hydro-4-alkoxy-2,6-di-tert-butylcyclohexa-2,5-dienones obtained by analogous means, however, have been successfully purified, and their structures have been unambiguously established. The results will be published elsewhere.
  • 23
    • 76049087331 scopus 로고    scopus 로고
    • Other reactions of 17 may be couplings with 8 and with atomic iodine (to give 12) (not shown in Scheme 3).
    • Other reactions of 17 may be couplings with 8 and with atomic iodine (to give 12) (not shown in Scheme 3).
  • 24
    • 76049128112 scopus 로고    scopus 로고
    • 2 (in mol) and half the content of product 2 (in mol) in that mixture.
    • 2 (in mol) and half the content of product 2 (in mol) in that mixture.
  • 28
    • 76049119929 scopus 로고    scopus 로고
    • In the workup of the reaction mixture, NaHSO3 (0.55 g) was employed
    • 3 (0.55 g) was employed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.