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Volumn 133, Issue 11, 1996, Pages 1127-1141

Carbophilic reactions of amines or methanol with thioaldehyde-S-oxides

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EID: 33746347089     PISSN: 00378968     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (5)

References (105)
  • 11
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    • b) Bull Soc Chim Fr (1996) 133, 515
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    • For a facile preparation of dialkyl disulfides from sulfur and alkyl halides under phase transfer conditions, see: Wang JX, Gui W, Hu Y
    • For a facile preparation of dialkyl disulfides from sulfur and alkyl halides under phase transfer conditions, see: Wang JX, Gui W, Hu Y, Synth Commun (1995) 25, 3573
    • (1995) Synth Commun , vol.25 , pp. 3573
  • 17
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    • See a recent improved procedure using bromine and sodium carbonate in methanol: Resek JE
    • Brownbridge P, Jowett 1C, Synthesis (1988) 252. See a recent improved procedure using bromine and sodium carbonate in methanol: Resek JE,
    • (1988) Synthesis , pp. 252
    • Brownbridge, P.1
  • 19
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    • While no pKa data have been determined, circumstantial evidence suggests that arenesulfenic acids ArSOH are at least as acidic as phenols, Barrett GC
    • (Patai S, ed), Wiley, Chichester The p/Va of 2-methylpropane-2-sulfenic acid is estimated as 10.47
    • While no pKa data have been determined, circumstantial evidence suggests that arenesulfenic acids ArSOH are at least as acidic as phenols, Barrett GC, in: The Chemistry of Sulphenic Acids and their Derivatives, (Patai S, ed), Wiley, Chichester (1990) 1. The p/Va of 2-methylpropane-2-sulfenic acid is estimated as 10.47:
    • (1990) The Chemistry of Sulphenic Acids and Their Derivatives , pp. 1
  • 21
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    • For some examples of acid- or micleophile-catalyzed cleavage of the S-O bond of sulfenic acid derivatives, see
    • For some examples of acid- or micleophile-catalyzed cleavage of the S-O bond of sulfenic acid derivatives, see:
  • 30
    • 0026756541 scopus 로고
    • Due to the lack of information concerning the salts NaSOH and NaSONa, they are probably unstable. See however scheme 22 in Block E
    • Due to the lack of information concerning the salts NaSOH and NaSONa, they are probably unstable. See however scheme 22 in Block E, Angew Chem Int Ed Engl (1992) 31, 1135;
    • (1992) Angew Chem Int Ed Engl , vol.31 , pp. 1135
  • 31
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    • 4
    • 4
  • 32
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    • Some a-oxothioamides RC(O)C(S)NR1R2 have been prepared by reaction of RC(O)CH(C1)SC1 with amines R'NHR2: Adividjaja G, Günther H, Voss J
    • It is likely that this transformation occurred through the intermediate compounds RC(O)CH(NR1R2)SX, X = Cl or NRXR2 by deprotonation in sequence with an elimination step
    • Some a-oxothioamides RC(O)C(S)NR1R2 have been prepared by reaction of RC(O)CH(C1)SC1 with amines R'NHR2: Adividjaja G, Günther H, Voss J, Liebigs Ann Chem (1983) 1116. It is likely that this transformation occurred through the intermediate compounds RC(O)CH(NR1R2)SX, X = Cl or NRXR2 by deprotonation in sequence with an elimination step
    • (1983) Liebigs Ann Chem , pp. 1116
  • 33
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    • It was reported that the self condensation of 2-methylpropane-2-sulfenic acid under alkaline conditions was much faster than under acidic conditions (ref 15)
    • It was reported that the self condensation of 2-methylpropane-2-sulfenic acid under alkaline conditions was much faster than under acidic conditions (ref 15):
  • 36
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    • See scheme 50A in ref [17]
    • See scheme 50A in ref [17]
  • 42
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    • The elimination of benzene- or methane-sulfenate anions from β-(arenesulfinyl)carbonyl compounds or from other sulfinylated substrates are easy in mild conditions
    • The elimination of benzene- or methane-sulfenate anions from β-(arenesulfinyl)carbonyl compounds or from other sulfinylated substrates are easy in mild conditions:
  • 49
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    • See also similar vinylogous eliminations affording conjugated dienones: Guittet E, Julia S
    • See also similar vinylogous eliminations affording conjugated dienones: Guittet E, Julia S, Synth Commun (1981) 11, 709 and 723
    • (1981) Synth Commun , vol.11
  • 50
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    • Similar oxathiiranes have been proposed for explaining the formation of ketones from thiokctones-S-oxides upon standing at room temperature: Le Nocher AM, Metzner P
    • Similar oxathiiranes have been proposed for explaining the formation of ketones from thiokctones-S-oxides upon standing at room temperature: Le Nocher AM, Metzner P, Tetrahedron Lett (1991) 32, 747
    • (1991) Tetrahedron Lett , vol.32 , pp. 747
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    • For the instability of some dithioacetal S-oxides, see
    • For the instability of some dithioacetal S-oxides, see:
  • 62
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    • 3 have been efficiently prepared by reaction of RC(O)CH(C1)SC1 with methanol and pyridine: Adividjaja G, Günther II
    • 3 have been efficiently prepared by reaction of RC(O)CH(C1)SC1 with methanol and pyridine: Adividjaja G, Günther II, Voss J, Angew Chem Int Ed Engl (1980) 19, 563;
    • (1980) Voss J, Angew Chem Int Ed Engl , vol.19 , pp. 563
  • 63
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    • See also a review: Oka K
    • 3 which are similar to the a-methoxysulfenic acid derivatives IXa
    • 3 which are similar to the a-methoxysulfenic acid derivatives IXa
    • Synthesis , vol.1981 , pp. 661
  • 64
    • 33746381055 scopus 로고    scopus 로고
    • A referee has suggested the possibility of the intermediate IXa being transformed via one or two steps, into a new unstable species ArCH(OCH3)OSM which finally should give easily the aldehydes 9
    • A referee has suggested the possibility of the intermediate IXa being transformed via one or two steps, into a new unstable species ArCH(OCH3)OSM which finally should give easily the aldehydes 9
  • 71
    • 84917975339 scopus 로고
    • It has been previously shown that the treatment of a cold solution of 2,2-dimethyl-l-(methylthio)but-3-ene1-thiol lithium salt in THF/H2O with an ethereal suspension of lithium methanesulfenate smoothly afforded the corresponding 2,2-dimethyl-l-(methylthio)but-3enyl methyl disulfide (60%): Ratovelomanana V, Huynh C, Julia S
    • It has been previously shown that the treatment of a cold solution of 2,2-dimethyl-l-(methylthio)but-3-ene1-thiol lithium salt in THF/H2O with an ethereal suspension of lithium methanesulfenate smoothly afforded the corresponding 2,2-dimethyl-l-(methylthio)but-3enyl methyl disulfide (60%): Ratovelomanana V, Huynh C, Julia S, CR Acad Sci, Paris (1975) 280C, 1327
    • (1975) CR Acad Sci, Paris , vol.280 , pp. 1327
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    • John Wiley and Sons, London
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    • Geissman, T.1
  • 74
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    • For 'H NMR data for other imines derivatives of benzylamine, see
    • For 'H NMR data for other imines derivatives of benzylamine, see:
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    • b) Bull Soc Chim Fr (1995) 132, 952
    • (1995) Bull Soc Chim Fr , vol.132 , pp. 952
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    • b) Bull Soc Chim Fr (1995) 132, 196
    • (1995) Bull Soc Chim Fr , vol.132 , pp. 196
  • 100
    • 33746350311 scopus 로고    scopus 로고
    • Several cases of base-catalyzed fragmentation of some disulfides affording thioaldehydes in situ have been described
    • Several cases of base-catalyzed fragmentation of some disulfides affording thioaldehydes in situ have been described:
  • 105
    • 0012005305 scopus 로고    scopus 로고
    • A very recent paper appeared recording a new transformation of some lithium or sodium arenemethanesulfinates in boiling water into the corresponding arenecarbaldehydes: Yoon SC, Kim K
    • A very recent paper appeared recording a new transformation of some lithium or sodium arenemethanesulfinates in boiling water into the corresponding arenecarbaldehydes: Yoon SC, Kim K, J Org Chem (1996) 61, 793
    • (1996) J Org Chem , vol.61 , pp. 793


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.