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Volumn 119, Issue 19, 1997, Pages 4525-4534

Chiral ions in the gas phase. 1. Intramolecular racemization and isomerization of O-protonated (S)-trans-4-hexen-3-ol

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL;

EID: 0030985945     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960212p     Document Type: Article
Times cited : (19)

References (52)
  • 15
    • 0000389099 scopus 로고
    • For reviews, see: (a) Samuel, D.; Silver, B. Adv. Phys. Org. Chem. 1965, 3, 128. (b) Raber, D. J.; Harris, J. M.; Schleyer, P. v. R. Ions and Ion Pairs in Organic Reactions Szwarc, M., Ed.; Wiley: New York, 1974; Vol. 2.
    • (1965) Adv. Phys. Org. Chem. , vol.3 , pp. 128
    • Samuel, D.1    Silver, B.2
  • 26
    • 0346521082 scopus 로고
    • Wiley: New York, Collect.
    • Coburn, E. R. Organic Syntheses; Wiley: New York, 1995; Collect. Vol. 3, p 696.
    • (1995) Organic Syntheses , vol.3 , pp. 696
    • Coburn, E.R.1
  • 41
    • 15144347631 scopus 로고    scopus 로고
    • note
    • -1, respectively.
  • 43
    • 15144359206 scopus 로고    scopus 로고
    • note
    • 16O displacement in closely related allylic alcohols (i.e., O-protonated 1-buten-3-ol and isomeric 2-buten-1-ols (ref 2).
  • 44
    • 15144338500 scopus 로고    scopus 로고
    • note
    • 18O-content from Tables 3 and 2 (see further in the text) does still express the relative efficiency of processes other than the intramolecular rearrangement iv of IS (Scheme 1), irrespective of whether they are unimolecular (path iii) or bimolecular (paths i and ii) in character.
  • 45
    • 15144361801 scopus 로고    scopus 로고
    • note
    • 3PO-induced bimolecular E2 and E2′ elimination in IS or in its ionic isomers. However, the conceivable interference from these bimolecular elimination processes does not affect the estimate of the rate constants of Table 5, provided that they occur to the same extent irrespective of the specific isomer (cf., ref 3c). In this case, in fact, occurrence of bimolecular E2 and E2′ eliminations may affect the absolute yields of the racemization and isomerization products, but not their relative distribution.
  • 47
    • 15144356509 scopus 로고    scopus 로고
    • note
    • -1 (temperature in °C) = 2.11 (40); 2.05 (70); 1.99 (100); 1.96 (120)).
  • 48
    • 15144350924 scopus 로고    scopus 로고
    • note
    • 2O] system), excludes the possibility of slow isomerization of the starting IS to IIR, followed by fast IIR → IIS racemization.
  • 49
    • 33847805365 scopus 로고
    • Kebarle and co-workers (Hiraoka, K.; Grimsrud, E. P.; Kebarle, P. J. Am. Chem. Soc. 1974, 96, 3359) demonstrated that replacement of a H atom by an alkyl group in an oxonium ion prevents hydrogen bonding on that position by n-type molecules and, thus, the buildup of the corresponding cluster.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 3359
    • Hiraoka, K.1    Grimsrud, E.P.2    Kebarle, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.