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Volumn 5, Issue 7, 2000, Pages 916-926

Novel behavior of thiiranium radical cation intermediates. Reactions of dimethyl disulfide with alkenes in the presence of Pd(OAc)2

Author keywords

Acetoxymethylthiolation; Dimethyl disulfide; Palladium (II) acetate; Regioselectivity for SN2 ring opening; Skeletal rearrangement; Solvent effects; Thietanium radical cation; Thiiranium radical cation

Indexed keywords

1 ACETOXY 2 METHYLCYCLOHEXANE; 1 ACETOXYMETHYL 2 METHYLTHIOCYCLOHEXANE; 1 METHYLCYCLOHEX 1 ENE; 2 METHYLPENT 1 ENE; ACTINIUM; ACTINIUM HYDROXIDE; ALKENE; ALKENE DERIVATIVE; CATION; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; DIMETHYL DISULFIDE; DISULFIDE; HEX 1 ENE; HEXANE; ION; PALLADIUM; PENTANE; RADICAL; SOLVENT; SULFONIUM DERIVATIVE; THIIRANIUM RADICAL; UNCLASSIFIED DRUG;

EID: 3342982314     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/50700916     Document Type: Article
Times cited : (2)

References (16)
  • 7
    • 0043227918 scopus 로고    scopus 로고
    • It has been reported that the disulfide radical cation is highly reactive in solution, regardless of whether it is generated by chemical, photochemical or electrochemical oxidation, and thus the spectral confirmation is difficult in solution; Marti, V.; Fernandez, L.; Garcia, H.; Roth, H. D. J. Chem. Soc., Perkin Trans. 2 1999, 145. We have recently observed that the disulfide radical cation (from MeSSMe) with λmax 375 nm is not capable of dissociation into a sulfenium ion, and undergoes an aromatic methylthiolation; the details will be published in the near future.
    • (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 145
    • Marti, V.1    Fernandez, L.2    Garcia, H.3    Roth, H.D.4
  • 8
    • 37049087013 scopus 로고
    • A sulfenium ion seems to be formed in the first instance, but this formation would be impossible because a very unstable sulfenium ion can be generated when it interacts directly with the unshared electron-pair of a compound formed by dissociation from the precursor; In fact, arylsufenium ions are generated by interaction with both the unshared electron-pair of amine and the counterion: Takeuchi, H.; Oya, H.; Yanase, T.; Itou, K.; Adachi, T.; Sugiura, H.; Hayashi, N. J. Chem. Soc., Perkin Trans. 2 1994, 827.
    • (1994) J. Chem. Soc., Perkin Trans. 2 , pp. 827
    • Takeuchi, H.1    Oya, H.2    Yanase, T.3    Itou, K.4    Adachi, T.5    Sugiura, H.6    Hayashi, N.7
  • 9
    • 85039487725 scopus 로고    scopus 로고
    • note
    • -OAc because of the formation of MeSAg.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.