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Volumn 56, Issue 11, 2008, Pages 1632-1634

Catalytic hypervalent iodine oxidation of p-dialkoxybenzenes to p-quinones using 4-iodophenoxyacetic acid and Oxone®

Author keywords

4 Iodophenoxyacetic acid; Blattellaquinone; Catalytic hypervalent iodine oxidation; Oxone ; p dialkoxybenzene; p quinone

Indexed keywords

4 IODOPHENOXYACETIC ACID; ALKYL GROUP; BLATTELLAQUINONE; IODINE DERIVATIVE; ORGANIC SOLVENT; PHENOXYACETIC ACID DERIVATIVE; QUINONE DERIVATIVE; SEX PHEROMONE; SODIUM PEROXIDE; TRIFLUOROETHANOL; UNCLASSIFIED DRUG; WATER;

EID: 55749100020     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.56.1632     Document Type: Article
Times cited : (34)

References (41)
  • 1
    • 84956614279 scopus 로고    scopus 로고
    • The Chemistry of the Quinonoid Compounds, 2, Parts 1 and 2, ed. by Patai S., Rappoport Z., John Wiley & Sons, Chichester, 1988.
    • "The Chemistry of the Quinonoid Compounds," Vol. 2, Parts 1 and 2, ed. by Patai S., Rappoport Z., John Wiley & Sons, Chichester, 1988.
  • 2
    • 55749083024 scopus 로고    scopus 로고
    • Naturally Occurring Quinones IV Recent Advances, ed. by Thomson R. H., Blackie Academic & Professional, London, 1997.
    • "Naturally Occurring Quinones IV Recent Advances," ed. by Thomson R. H., Blackie Academic & Professional, London, 1997.
  • 3
    • 0006473433 scopus 로고
    • ed. by Trost B. M, Fleming I, Elsevier, Oxford
    • Dudfield P. J., "Comprehensive Organic Synthesis," Vol. 7, ed. by Trost B. M., Fleming I., Elsevier, Oxford, 1991, pp. 345-356.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 345-356
    • Dudfield, P.J.1
  • 11
    • 55749114192 scopus 로고    scopus 로고
    • Hypervalent Iodine in Organic Synthesis, ed. by Varvoglis A., Academic Press, San Diego, 1997.
    • "Hypervalent Iodine in Organic Synthesis," ed. by Varvoglis A., Academic Press, San Diego, 1997.
  • 12
    • 0032821239 scopus 로고    scopus 로고
    • Review
    • Review: Wirth T., Hirt U. H., Synthesis, 1999, 1271-1287 (1999).
    • (1999) Synthesis , vol.1999 , pp. 1271-1287
    • Wirth, T.1    Hirt, U.H.2
  • 16
    • 33746303252 scopus 로고    scopus 로고
    • Review
    • Review: Dohi T., Kita Y., Kagaku, 61, 68-69 (2006).
    • (2006) Kagaku , vol.61 , pp. 68-69
    • Dohi, T.1    Kita, Y.2
  • 31
    • 55749091573 scopus 로고    scopus 로고
    • Typical reaction procedure: Compound 1 (0.050 mmol) was added to a solution of 2 (1.0 mmol) in CF3CH2OH-H 2O (1:2, 10 ml, followed by Oxone® (4 mmol) at room temperature, the resulting mixture was stirred at the same temperature. After 2 was consumed completely, as indicated by TLC, the mixture was diluted with ethyl acetate and washed with water. The organic layer was then washed with aqueous saturated sodium bicarbonate solution and dried, then concentrated to give pure 3. If necessary, the product was purified using column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and dried, then concentrated to recover 1 75-85, which was purified by recrystallization from diethyl ether-hexane. All new compounds gave satisfactory spectrospecific
    • 2O (1:2, 10 ml), followed by Oxone® (4 mmol) at room temperature, the resulting mixture was stirred at the same temperature. After 2 was consumed completely, as indicated by TLC, the mixture was diluted with ethyl acetate and washed with water. The organic layer was then washed with aqueous saturated sodium bicarbonate solution and dried, then concentrated to give pure 3. If necessary, the product was purified using column chromatography on silica gel to give pure quinone. The alkaline solution was acidified by 10% hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and dried, then concentrated to recover 1 (75-85%) which was purified by recrystallization from diethyl ether-hexane. All new compounds gave satisfactory spectrospecific data.
  • 32
    • 55749096728 scopus 로고    scopus 로고
    • 2O showed no presence of hypervalent iodine species.
    • 2O showed no presence of hypervalent iodine species.
  • 33
    • 55749089526 scopus 로고    scopus 로고
    • Many reports for the formation of hypervalent iodine species by the oxidation of iodoarene with Oxone® have appeared.36-41
    • 36-41)
  • 34
    • 55749098770 scopus 로고    scopus 로고
    • 4: 222.08921).
    • 4: 222.08921).
  • 35
    • 55749092110 scopus 로고    scopus 로고
    • Although Nojima et al. reported oxidation of 8 with CAN, that report includes no description related to detailed reaction conditions and yield.7
    • 7)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.