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Volumn 64, Issue 16, 1999, Pages 5826-5831

Reactions of 2-iodo- and 1,2-dihaloadamantanes with carbanions in DMSO by the S(RN)1 mechanism

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHALOADAMANTANE; 2 IODOADAMANTANE; ADAMANTANE DERIVATIVE; ALKYL GROUP; DIMETHYL SULFOXIDE; HALIDE; UNCLASSIFIED DRUG;

EID: 0033529732     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990156l     Document Type: Article
Times cited : (22)

References (65)
  • 1
    • 0000057584 scopus 로고
    • Tanner, D. D., Ed.; Jai Press
    • For reviews, see: (a) Rossi, R. A.; Pierini A. B.; Palacios, S. M. Advances in Free Radical Chemistry; Tanner, D. D., Ed.; Jai Press: 1990; p 193; J. Chem. Ed. 1989, 66, 720. (b) Rossi, R. A.; Pierini A. B.; Peñéñory, A.B. The Chemistry of Functional Group; Patai S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Supl. D2, Chapter 24, p 1395.
    • (1990) Advances in Free Radical Chemistry , pp. 193
    • Rossi, R.A.1    Pierini, A.B.2    Palacios, S.M.3
  • 2
    • 0344931125 scopus 로고
    • For reviews, see: (a) Rossi, R. A.; Pierini A. B.; Palacios, S. M. Advances in Free Radical Chemistry; Tanner, D. D., Ed.; Jai Press: 1990; p 193; J. Chem. Ed. 1989, 66, 720. (b) Rossi, R. A.; Pierini A. B.; Peñéñory, A.B. The Chemistry of Functional Group; Patai S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Supl. D2, Chapter 24, p 1395.
    • (1989) J. Chem. Ed. , vol.66 , pp. 720
  • 3
    • 0001300928 scopus 로고
    • Patai S., Rappoport, Z., Eds.; Wiley: Chichester, Chapter 24
    • For reviews, see: (a) Rossi, R. A.; Pierini A. B.; Palacios, S. M. Advances in Free Radical Chemistry; Tanner, D. D., Ed.; Jai Press: 1990; p 193; J. Chem. Ed. 1989, 66, 720. (b) Rossi, R. A.; Pierini A. B.; Peñéñory, A.B. The Chemistry of Functional Group; Patai S., Rappoport, Z., Eds.; Wiley: Chichester, 1995; Supl. D2, Chapter 24, p 1395.
    • (1995) The Chemistry of Functional Group , Issue.SUPL. D2 , pp. 1395
    • Rossi, R.A.1    Pierini, A.B.2    Peñéñory, A.B.3
  • 23
    • 0003279562 scopus 로고
    • RN1 Mechanism
    • American Chemical Society: Washington, D.C.
    • RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, D.C., 1983. (b) Rossi, R. A. Acc. Chem. Res. 1982, 15, 164. (c) Norris, R. K. Compr. Org. Synth. 1991, 4, 451.
    • (1983) ACS Monograph , vol.178
    • Rossi, R.A.1    De Rossi, R.H.2
  • 24
    • 33845554901 scopus 로고
    • RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, D.C., 1983. (b) Rossi, R. A. Acc. Chem. Res. 1982, 15, 164. (c) Norris, R. K. Compr. Org. Synth. 1991, 4, 451.
    • (1982) Acc. Chem. Res. , vol.15 , pp. 164
    • Rossi, R.A.1
  • 25
    • 0000866608 scopus 로고
    • RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, D.C., 1983. (b) Rossi, R. A. Acc. Chem. Res. 1982, 15, 164. (c) Norris, R. K. Compr. Org. Synth. 1991, 4, 451.
    • (1991) Compr. Org. Synth. , vol.4 , pp. 451
    • Norris, R.K.1
  • 53
    • 24544441446 scopus 로고
    • Estimation of the steric bulk of the trimethyltin group indicates that it is very similar to that of the chlorine and smaller than bromine groups. See: Davis, D. D.; Surmatis, A. J.; Robertson, G. L. J. Organomet. Chem. 1972, 46, C9.
    • (1972) J. Organomet. Chem. , vol.46
    • Davis, D.D.1    Surmatis, A.J.2    Robertson, G.L.3
  • 57
    • 0344068940 scopus 로고    scopus 로고
    • note
    • a for the coupling process between adamantyl radicals and 6 are as follows: 17.1 kcal/mol and 10.82 kcal/ mol for the 2- and 1-adamantyl radicals, respectively. The calculations were carried out with the AM1 method.
  • 59
    • 0344931120 scopus 로고    scopus 로고
    • note
    • Small amount of unidentified olefins were found.
  • 60
    • 0344931121 scopus 로고    scopus 로고
    • note
    • Compound 21a was formed in major proportion, with mere traces of 21b. These two compounds were quantified together; 21a was purified and the structure determined.
  • 61
    • 0344068939 scopus 로고    scopus 로고
    • note
    • There was no reaction of 20 with 2 in the dark (3 h), but under irradiation there was a very fast process (5 min) which gave 15 in low yield (28%) although iodide ions were quantified to be 162%. The reaction was inhibited by p-DNB. There were substantial amounts of several unidentified olefins. These reactions were not studied further.
  • 62
    • 0344500062 scopus 로고    scopus 로고
    • note
    • The LUMO value of 20 is 0.149 eV, compared with 1-IAd (0.446 eV) and 1 (0.523 eV) (AM1 method).
  • 65
    • 0344068938 scopus 로고    scopus 로고
    • note
    • The HRMS could not be determined by EI or FAB.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.