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Volumn 63, Issue 23, 1998, Pages 8515-8521

Multilevel selectivity in the mild and high-yielding chlorosilane- induced cleavage of carbamates to isocyanates

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID; ISOCYANATE; SILANE;

EID: 0032514855     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981816+     Document Type: Article
Times cited : (56)

References (62)
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    • In most cases where trimethylchlorosilane was used, considerable heating was required to generate the isocyanate. (a) Greber, G.; Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1968, 7, 941. (b) Kricheldorf, H. R. Angew. Chem. 1972, 84, 107. (c) Kricheldorf, H. R. Synthesis 1970, 649. (d) Kricheldorf, H. R. Liebigs Ann. Chem. 1973, 772. (e) Kricheldorf, H. R. Chem. Ber. 1971, 104, 3146.
    • (1968) Angew. Chem., Int. Ed. Engl. , vol.7 , pp. 941
    • Greber, G.1    Kricheldorf, H.R.2
  • 14
    • 84981826650 scopus 로고
    • In most cases where trimethylchlorosilane was used, considerable heating was required to generate the isocyanate. (a) Greber, G.; Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1968, 7, 941. (b) Kricheldorf, H. R. Angew. Chem. 1972, 84, 107. (c) Kricheldorf, H. R. Synthesis 1970, 649. (d) Kricheldorf, H. R. Liebigs Ann. Chem. 1973, 772. (e) Kricheldorf, H. R. Chem. Ber. 1971, 104, 3146.
    • (1972) Angew. Chem. , vol.84 , pp. 107
    • Kricheldorf, H.R.1
  • 15
    • 85065120278 scopus 로고
    • In most cases where trimethylchlorosilane was used, considerable heating was required to generate the isocyanate. (a) Greber, G.; Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1968, 7, 941. (b) Kricheldorf, H. R. Angew. Chem. 1972, 84, 107. (c) Kricheldorf, H. R. Synthesis 1970, 649. (d) Kricheldorf, H. R. Liebigs Ann. Chem. 1973, 772. (e) Kricheldorf, H. R. Chem. Ber. 1971, 104, 3146.
    • (1970) Synthesis , pp. 649
    • Kricheldorf, H.R.1
  • 16
    • 84913634192 scopus 로고
    • In most cases where trimethylchlorosilane was used, considerable heating was required to generate the isocyanate. (a) Greber, G.; Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1968, 7, 941. (b) Kricheldorf, H. R. Angew. Chem. 1972, 84, 107. (c) Kricheldorf, H. R. Synthesis 1970, 649. (d) Kricheldorf, H. R. Liebigs Ann. Chem. 1973, 772. (e) Kricheldorf, H. R. Chem. Ber. 1971, 104, 3146.
    • (1973) Liebigs Ann. Chem. , pp. 772
    • Kricheldorf, H.R.1
  • 17
    • 84899914831 scopus 로고
    • In most cases where trimethylchlorosilane was used, considerable heating was required to generate the isocyanate. (a) Greber, G.; Kricheldorf, H. R. Angew. Chem., Int. Ed. Engl. 1968, 7, 941. (b) Kricheldorf, H. R. Angew. Chem. 1972, 84, 107. (c) Kricheldorf, H. R. Synthesis 1970, 649. (d) Kricheldorf, H. R. Liebigs Ann. Chem. 1973, 772. (e) Kricheldorf, H. R. Chem. Ber. 1971, 104, 3146.
    • (1971) Chem. Ber. , vol.104 , pp. 3146
    • Kricheldorf, H.R.1
  • 18
    • 0001535945 scopus 로고
    • The use of trichlorosilane requires less heating than that of chlorotrimethylsilane. (a) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2781. (b) Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904. (c) Pirkle, W, H,; Rinaldi, P. L. J. Org. Chem. 1978, 43, 3803.
    • (1977) J. Org. Chem. , vol.42 , pp. 2781
    • Pirkle, W.H.1    Hauske, J.R.2
  • 19
    • 0001176348 scopus 로고
    • The use of trichlorosilane requires less heating than that of chlorotrimethylsilane. (a) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2781. (b) Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904. (c) Pirkle, W, H,; Rinaldi, P. L. J. Org. Chem. 1978, 43, 3803.
    • (1974) J. Org. Chem. , vol.39 , pp. 3904
    • Pirkle, W.H.1    Hoekstra, M.S.2
  • 20
    • 0000098337 scopus 로고
    • The use of trichlorosilane requires less heating than that of chlorotrimethylsilane. (a) Pirkle, W. H.; Hauske, J. R. J. Org. Chem. 1977, 42, 2781. (b) Pirkle, W. H.; Hoekstra, M. S. J. Org. Chem. 1974, 39, 3904. (c) Pirkle, W, H,; Rinaldi, P. L. J. Org. Chem. 1978, 43, 3803.
    • (1978) J. Org. Chem. , vol.43 , pp. 3803
    • Pirkle, W.H.1    Rinaldi, P.L.2
  • 22
    • 15644379935 scopus 로고    scopus 로고
    • note
    • The traditional reaction conditions employ chlorotrimethylsilane and high reaction temperatures (>100 °C). See ref 9.
  • 23
    • 15644371400 scopus 로고    scopus 로고
    • note
    • Although accurate quantitative information was not obtained, the GC-MS traces provided us with estimates of the progress of reaction.
  • 24
    • 15644376766 scopus 로고    scopus 로고
    • note
    • 1H NMR since the substrates react with isobutylamine.
  • 25
    • 15644373730 scopus 로고    scopus 로고
    • note
    • Isocyanates were derivatized by reaction with isobutylamine.
  • 26
    • 15644366268 scopus 로고    scopus 로고
    • note
    • Reactions of biscarbamates 7b-d were carried out in chloroform due to their poor solubilities in benzene.
  • 27
    • 15644371758 scopus 로고    scopus 로고
    • note
    • The trichloroethoxycarbonyl group is easily removed by reduction with zinc metal in acetic acid or hot ethanol. See refs 1 and 3.
  • 31
    • 15644362804 scopus 로고    scopus 로고
    • note
    • 2O.
  • 32
    • 15644369397 scopus 로고
    • ICI Ltd. Patent, DE 2254611
    • (a) ICI Ltd. Patent, DE 2254611; Chem. Abstr. 1973, 79, 65996.
    • (1973) Chem. Abstr. , vol.79 , pp. 65996
  • 50
    • 15644369167 scopus 로고    scopus 로고
    • Patent, DE 817461, 1948
    • Merck, E. Patent, DE 817461, 1948.
    • Merck, E.1
  • 55
  • 58
    • 0010704566 scopus 로고
    • The spectroscopic data were in agreement with the references: (a) Le Corre, M.; Hercouet, A.; Le Stanc, Y.; Le Baron, H. Tetrahedron 1985, 41, 5313. (b) Aboujaoude, E. E.; Collignon, N.; Savignac, P. Tetrahedron 1986, 41, 427.
    • (1985) Tetrahedron , vol.41 , pp. 5313
    • Le Corre, M.1    Hercouet, A.2    Le Stanc, Y.3    Le Baron, H.4
  • 59
    • 0021928653 scopus 로고
    • The spectroscopic data were in agreement with the references: (a) Le Corre, M.; Hercouet, A.; Le Stanc, Y.; Le Baron, H. Tetrahedron 1985, 41, 5313. (b) Aboujaoude, E. E.; Collignon, N.; Savignac, P. Tetrahedron 1986, 41, 427.
    • (1986) Tetrahedron , vol.41 , pp. 427
    • Aboujaoude, E.E.1    Collignon, N.2    Savignac, P.3
  • 60
    • 15644374758 scopus 로고    scopus 로고
    • note
    • 3 and was not fully stable with more polar solvents.
  • 62
    • 15644374203 scopus 로고    scopus 로고
    • note
    • The short reaction time was necessary to prevent isobutylamine from reacting with the p-methoxyphenyl carbamate, which would have resulted in formation of the bis-urea.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.