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Volumn 126, Issue 20, 2004, Pages 6356-6362

Oxidation of alkylarenes by nitrate catalyzed by polyoxophosphomolybdates: Synthetic applications and mechanistic insights

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CATALYSIS; CHARGE TRANSFER; INFRARED RADIATION; OXIDATION; SALTS;

EID: 2442697671     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031710i     Document Type: Article
Times cited : (37)

References (88)
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    • (1978) Oxidation in Organic Chemistry, Part C , pp. 295-342
    • Ogata, Y.1
  • 4
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    • Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester
    • (d) Bosch, E.; Kochi, J. K. In N-Centered Radicals; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, 1998; pp 69-128.
    • (1998) N-Centered Radicals , pp. 69-128
    • Bosch, E.1    Kochi, J.K.2
  • 28
    • 0004170617 scopus 로고    scopus 로고
    • Kluwer Academic: Dordrecht, The Netherlands
    • (b) Müller, A. Polyoxometalate Chemistry; Kluwer Academic: Dordrecht, The Netherlands, 2001.
    • (2001) Polyoxometalate Chemistry
    • Müller, A.1
  • 67
    • 0142061096 scopus 로고    scopus 로고
    • Recently, there has been a report on the oxidation of sulfides to sulfoxides catalyzed by polyoxometalate/nitrate catalysts: Okun, N. M.; Anderson, T. M.; Hardcastle, K. I.; Hill, C. L. Inorg. Chem. 2003, 42, 6610-6612.
    • (2003) Inorg. Chem. , vol.42 , pp. 6610-6612
    • Okun, N.M.1    Anderson, T.M.2    Hardcastle, K.I.3    Hill, C.L.4
  • 69
    • 2442657283 scopus 로고    scopus 로고
    • note
    • 2.
  • 71
    • 2442639726 scopus 로고    scopus 로고
    • note
    • 3.
  • 72
    • 2442648486 scopus 로고    scopus 로고
    • note
    • 18O as measured by GC-MS.
  • 73
    • 2442653471 scopus 로고    scopus 로고
    • Taken from the NIST database at http://webbook.nist.gov/chemistry.
  • 76
    • 2442657284 scopus 로고    scopus 로고
    • note
    • 40.
  • 77
    • 2442647187 scopus 로고    scopus 로고
    • note
    • B.
  • 78
    • 0002470963 scopus 로고    scopus 로고
    • Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester
    • There was no significant homocoupling of benzylic radicals to yield dimeric dibenzylic products. See also: Weiner, B.; Barhard, K. I. N-Centered Radicals; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, 1998; pp 39-67.
    • (1998) N-Centered Radicals , pp. 39-67
    • Weiner, B.1    Barhard, K.I.2
  • 79
    • 2442688614 scopus 로고    scopus 로고
    • note
    • In a separate reaction it was shown that 1-pentylnitrite reacts immediately in acetic acid to yield mostly >95% 1-pentanol.
  • 80
    • 2442677293 scopus 로고    scopus 로고
    • note
    • A referee suggested the possibility of fast further oxidation of the benzylic radical to a benzyl cation followed by reaction of the benzylic cation with nitrate to yield benyzl nitrate. We found no evidence for formation of nitrate esters that have some stability under reaction conditions. Also this pathway is not compatible with the results observed for the oxidation of phenylcyclopropane (see below).
  • 81
    • 0037321476 scopus 로고    scopus 로고
    • and references therein
    • The oxidation of benzylic alcohols with nitric acid is known; cf. Strazzolini, P.; Runcio, A. Eur. J. Org. Chem. 2003, 526-536 and references therein.
    • (2003) Eur. J. Org. Chem. , pp. 526-536
    • Strazzolini, P.1    Runcio, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.