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Volumn 84, Issue 1, 2011, Pages 577-585

Regioselective α-Monochlorination of N-protected-3-piperidones

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EID: 84855967879     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-S(P)23     Document Type: Article
Times cited : (4)

References (48)
  • 1
    • 12344313515 scopus 로고
    • For reviews of nitrosoalkenes and lead references see
    • For reviews of nitrosoalkenes and lead references see: a) T. L. Gilchrist, Chem. Soc. Rev., 1983, 11, 53
    • (1983) Chem. Soc. Rev. , vol.11 , pp. 53
    • Gilchrist, T.L.1
  • 3
    • 0001693820 scopus 로고
    • For some other examples of enolonium ion equivalents see
    • For some other examples of enolonium ion equivalents see: a) P. L. Fuchs, J. Org. Chem., 1976, 41, 2935
    • (1976) J. Org. Chem. , vol.41 , pp. 2935
    • Fuchs, P.L.1
  • 33
    • 84855943870 scopus 로고    scopus 로고
    • Although it is possible, in principle, to use α-bromoketones to prepare nitrosoalkenes via !-bromooxime precursors, we have found that the α-bromoketones tend to produce significant amounts of elimination and halogen-displacement products under standard oximation conditions
    • Although it is possible, in principle, to use α-bromoketones to prepare nitrosoalkenes via !-bromooxime precursors, we have found that the α-bromoketones tend to produce significant amounts of elimination and halogen-displacement products under standard oximation conditions.
  • 38
    • 84855939089 scopus 로고
    • Sulfuryl chloride readily decomposes to sulfur dioxide and chlorine on standing
    • Sulfuryl chloride readily decomposes to sulfur dioxide and chlorine on standing: D. F. Smith, J. Am. Chem. Soc., 1925, 47, 1862.
    • (1925) J. Am. Chem. Soc. , vol.47 , pp. 1862
    • Smith, D.F.1
  • 40
    • 84855939087 scopus 로고    scopus 로고
    • 1H NMR spectra of some of the chromatographically purified !-chloropiperidone products are still complex due to keto-enol tautomerization. However, in these cases we have found that adding 1 drop of trifluoroacetic acid to the NMR solvent produces clean spectra of the !-chloroketones in the keto-form
    • 1H NMR spectra of some of the chromatographically purified !-chloropiperidone products are still complex due to keto-enol tautomerization. However, in these cases we have found that adding 1 drop of trifluoroacetic acid to the NMR solvent produces clean spectra of the !-chloroketones in the keto-form.
  • 41
    • 84855939090 scopus 로고    scopus 로고
    • N-SES-3-Piperidone (16) is a known compound (see ref. 7a) but no details of its synthesis were reported
    • N-SES-3-Piperidone (16) is a known compound (see ref. 7a) but no details of its synthesis were reported.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.