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Volumn 126, Issue 29, 2004, Pages 9085-9093

Reversible disulfur monoxide (S2O)-forming retro-Diels-Alder reaction. Disproportionation of S2O to trithio-ozone (S3) and sulfur dioxide (SO2) and reactivities of S2O and S3

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; ISOMERIZATION; ISOMERS; MIXTURES; ORGANIC COMPOUNDS; OXIDATION; THERMAL EFFECTS;

EID: 3242744396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047729i     Document Type: Article
Times cited : (36)

References (90)
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    • (a) Hapke, B. Icarus 1989, 79, 56-74.
    • (1989) Icarus , vol.79 , pp. 56-74
    • Hapke, B.1
  • 32
    • 3242749236 scopus 로고    scopus 로고
    • note
    • 13g The two 1,4-cis-mode bromine adducts (syn- and anti-adducts to the S=O bond) to 3 are stable enough to be isolated by usual methods (silica gel column chromatography and crystallization). Therefore, the SSCl group of 7 plays a crucial role to the mutual conversion between the two species, and the carbenium ion 14b would not be a probable intermediate.
  • 35
    • 3242759275 scopus 로고    scopus 로고
    • note
    • 13g
  • 37
    • 0003940737 scopus 로고
    • Academic Press: New York, and references therein
    • For neighboring group participation of sulfur, see Block, E. Reactions of Organosulfur Compounds, Academic Press: New York, 1978; pp 141-145, and references therein.
    • (1978) Reactions of Organosulfur Compounds , pp. 141-145
    • Block, E.1
  • 44
    • 0000062443 scopus 로고
    • 1H NMR spectra of the equilibrating systems, see cycloheptatriene-norcaradiene system: (a) Vogel, E.; Wendisch, D.; Roth, W. R. Angew. Chem. 1964, 76, 432-433.
    • (1964) Angew. Chem. , vol.76 , pp. 432-433
    • Vogel, E.1    Wendisch, D.2    Roth, W.R.3
  • 46
    • 0002342570 scopus 로고
    • (c) Ciganek, E. J. Am. Chem. Soc. 1967, 89, 1458-1468. Benzene oxide-oxepin system:
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 1458-1468
    • Ciganek, E.1
  • 73
    • 3242742365 scopus 로고    scopus 로고
    • note
    • The calculations were carried out at both B3LYP/6-311+G(d) and B3LYP/6-311+G(3df) levels, although the results of the latter level calculations are described here; for the former level calculations and the vibrational models and frequencies of these molecules, see Supporting Information.
  • 76
    • 3242791964 scopus 로고    scopus 로고
    • note
    • -1 exothermic.
  • 77
    • 11744326736 scopus 로고
    • Padwa, A., Ed.; John Wiley: New York, Chapter 1
    • (a) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley: New York, 1983; Vol. 1, Chapter 1.
    • (1983) 1,3-Dipolar Cycloaddition Chemistry , vol.1
    • Huisgen, R.1
  • 83
    • 0000028936 scopus 로고
    • For the exo-selection and enhanced reactivities of norbornene, see (a) Schleyer, P. von R. J. Am Chem. Soc. 1967, 89, 701-703.
    • (1967) J. Am Chem. Soc. , vol.89 , pp. 701-703
    • Schleyer, P.V.R.1
  • 87
    • 3242773963 scopus 로고    scopus 로고
    • note
    • 1H NMR data of 25.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.