1968
DOI: 10.1139/v68-613
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Stéréochimie de l'époxydation du tert-butyl-3 cyclohexène

Abstract: Canadian Journal of Chemistry, 46, 3709 (1968) Introduction A la suite de travaux (1-3) qui nous ont amen6 aexaminer lastCrCochimie, dela rCaction d'Cpoxydation de doubles liaisons faisant partie de cycles, il nous est apparu intCressant pour fins de comparaison d'examiner la stCrCochimie de 1'Cpoxydation du tert-butyl-3 cyclohexbne (1). Les rCsultats obtenus au cours de cette Ctude font l'objet de la prCsente communication. RCsultats et DiscussionL'alcene examink (1) a Ct C prCparC pratiquement pur par pyr… Show more

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Cited by 13 publications
(5 citation statements)
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“…group in the pseudo-axial position for 3b and pseudo-equa-Dimethyldioxirane (DMD) [18] and methyltrioxorhenium (MTO) [19] were prepared according to literature procedures, as were also the torial for 3c. As for the flexible 2-cycloalkenols 2, 3a, 4, 3-alkyl-substituted cyclohexenes 1b, [20] 1c, [21] and 1d [22] and the and 5, the oxidation of the rigid 3b, c by MTO/UHP also conformationally fixed cis-and trans-5-tert-butyl-2-cyclohexenols proceeded cleanly in good yields to the syn-and anti-epox-(3b, c). [23] The cyclic alcohols 2-cyclopentenol (2), [24] 2-cyclohexides 8b, c without any enone formation (Table 3, Entries 1, enol (3a), [25] and 2-cyclooctenol (5) [26] were synthesized by pho-3, 7, 9).…”
Section: Methodsmentioning
confidence: 96%
See 1 more Smart Citation
“…group in the pseudo-axial position for 3b and pseudo-equa-Dimethyldioxirane (DMD) [18] and methyltrioxorhenium (MTO) [19] were prepared according to literature procedures, as were also the torial for 3c. As for the flexible 2-cycloalkenols 2, 3a, 4, 3-alkyl-substituted cyclohexenes 1b, [20] 1c, [21] and 1d [22] and the and 5, the oxidation of the rigid 3b, c by MTO/UHP also conformationally fixed cis-and trans-5-tert-butyl-2-cyclohexenols proceeded cleanly in good yields to the syn-and anti-epox-(3b, c). [23] The cyclic alcohols 2-cyclopentenol (2), [24] 2-cyclohexides 8b, c without any enone formation (Table 3, Entries 1, enol (3a), [25] and 2-cyclooctenol (5) [26] were synthesized by pho-3, 7, 9).…”
Section: Methodsmentioning
confidence: 96%
“…The (0°C/50 mbar), the crude material was purified by flash chromatogquantitative product data are given in Tables 1Ϫ3. raphy over [10] 6b, [10] 6d, [9] [10] 7, [29] 8a, [10] [31] and the enones 11, [32] 12a, [33] 12b, [6c] 13, [34] and 14 [35] were…”
Section: -Cycloheptenol (4)mentioning
confidence: 99%
“…Since the para C-H dipole and the Li-0 quadrupole axis are not parallel, rapid internal rotation would lead to an apparently smaller rc and produce a larger QSC on substitution in eq 10. 24 Both effects may be operating.…”
mentioning
confidence: 99%
“…3- tert -Butylcyclohexene (2m) was synthesized by reaction of 2- tert -butylcyclohexanone tosylhydrazone and n -butyllithium according to the literature method …”
Section: Methodsmentioning
confidence: 99%