메뉴 건너뛰기




Volumn 120-121, Issue , 1997, Pages 41-59

The sulfur diatomics: Generation and trapping chemistry

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0031483040     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426509708545509     Document Type: Article
Times cited : (21)

References (114)
  • 2
    • 0004098344 scopus 로고    scopus 로고
    • May 6, nitric oxide was twice voted "Molecule of the Year" by the American Association for the Advancement of Science (1992 and 1993);
    • a) The Chemical and Engineering News, May 6, 1996, p. 38; nitric oxide was twice voted "Molecule of the Year" by the American Association for the Advancement of Science (1992 and 1993);
    • (1996) The Chemical and Engineering News , pp. 38
  • 10
    • 0003841052 scopus 로고
    • Washington, DC, October 24
    • The Washington Post, Washington, DC, October 24, 1994 p A3.
    • (1994) The Washington Post
  • 12
    • 0041020138 scopus 로고
    • Ph.D. thesis, University of Arizona, Professor Richard Glass, supervisor, University Microfilms, Ann Arbor, MI, 77-11, 451
    • A number of imaginative attempts to generate diatomic sulfur were carried out in a Ph.D. thesis in 1976 by D. L. Smith, (University of Arizona, Professor Richard Glass, supervisor), University Microfilms, Ann Arbor, MI, 77-11, 451.
    • (1976)
    • Smith, D.L.1
  • 13
    • 0000736856 scopus 로고
    • K. Steliou, Y. Gareau and D. N. Harpp, J. Am. Chem. Soc., 106, 799 (1984). Diatomic sulfur loss has also been implicated in a monothioozonide, M. G. Matturro, R. P. Reynolds, R. V. Kastrup and C. F. Pictroski, J. Am. Chem. Soc., 108, 2775 (1986). The stereochemistry of this addition has been investigated, K. Steliou, Y. Gareau, G. Milot and P. Salama, J. Am. Chem. Soc., 112, 7819 (1990).
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 799
    • Steliou, K.1    Gareau, Y.2    Harpp, D.N.3
  • 14
    • 0001619246 scopus 로고
    • K. Steliou, Y. Gareau and D. N. Harpp, J. Am. Chem. Soc., 106, 799 (1984). Diatomic sulfur loss has also been implicated in a monothioozonide, M. G. Matturro, R. P. Reynolds, R. V. Kastrup and C. F. Pictroski, J. Am. Chem. Soc., 108, 2775 (1986). The stereochemistry of this addition has been investigated, K. Steliou, Y. Gareau, G. Milot and P. Salama, J. Am. Chem. Soc., 112, 7819 (1990).
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2775
    • Matturro, M.G.1    Reynolds, R.P.2    Kastrup, R.V.3    Pictroski, C.F.4
  • 15
    • 2042437127 scopus 로고
    • K. Steliou, Y. Gareau and D. N. Harpp, J. Am. Chem. Soc., 106, 799 (1984). Diatomic sulfur loss has also been implicated in a monothioozonide, M. G. Matturro, R. P. Reynolds, R. V. Kastrup and C. F. Pictroski, J. Am. Chem. Soc., 108, 2775 (1986). The stereochemistry of this addition has been investigated, K. Steliou, Y. Gareau, G. Milot and P. Salama, J. Am. Chem. Soc., 112, 7819 (1990).
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7819
    • Steliou, K.1    Gareau, Y.2    Milot, G.3    Salama, P.4
  • 16
    • 0000877306 scopus 로고
    • A. Orahovatiz, M. I. Levinson, P. J. Carroll, M. V. Lakshmikanthan and M. P. Cava, J. Org. Chem., 50, 1550 (1985); a somewhat related example was reported which resulted in the detection of a Diels-Alder adduct with diene 15b, but no isolation was achieved; see J. E. Bishop, S. A. Dagham and H. Rapoport, J. Org. Chem., 54, 1876 (1989).
    • (1985) J. Org. Chem. , vol.50 , pp. 1550
    • Orahovatiz, A.1    Levinson, M.I.2    Carroll, P.J.3    Lakshmikanthan, M.V.4    Cava, M.P.5
  • 17
    • 0000411294 scopus 로고
    • A. Orahovatiz, M. I. Levinson, P. J. Carroll, M. V. Lakshmikanthan and M. P. Cava, J. Org. Chem., 50, 1550 (1985); a somewhat related example was reported which resulted in the detection of a Diels-Alder adduct with diene 15b, but no isolation was achieved; see J. E. Bishop, S. A. Dagham and H. Rapoport, J. Org. Chem., 54, 1876 (1989).
    • (1989) J. Org. Chem. , vol.54 , pp. 1876
    • Bishop, J.E.1    Dagham, S.A.2    Rapoport, H.3
  • 25
    • 0001267833 scopus 로고
    • K. C. Nicolaou, C.-K. Hwang, M. E. Duggan and P. J. Carroll, J. Am. Chem. Soc., 109, 3801 (1987); K. C. Nicolaou, C.-K. Hwang, S. DeFrees and N. Stylianides, J. Am. Chem. Soc., 110, 4868 (1988); K. C. Nicolaou, S. A. DeFrees, C.-K. Hwang, N. Stylianides, P. J. Carroll and J. P. Snyder, J. Am. Chem. Soc., 112, 3029 (1990). It should be pointed out that this is the only example of a stable, saturated 1,2-dithietane ring system.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3801
    • Nicolaou, K.C.1    Hwang, C.-K.2    Duggan, M.E.3    Carroll, P.J.4
  • 26
    • 33845278183 scopus 로고
    • K. C. Nicolaou, C.-K. Hwang, M. E. Duggan and P. J. Carroll, J. Am. Chem. Soc., 109, 3801 (1987); K. C. Nicolaou, C.-K. Hwang, S. DeFrees and N. Stylianides, J. Am. Chem. Soc., 110, 4868 (1988); K. C. Nicolaou, S. A. DeFrees, C.-K. Hwang, N. Stylianides, P. J. Carroll and J. P. Snyder, J. Am. Chem. Soc., 112, 3029 (1990). It should be pointed out that this is the only example of a stable, saturated 1,2-dithietane ring system.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4868
    • Nicolaou, K.C.1    Hwang, C.-K.2    DeFrees, S.3    Stylianides, N.4
  • 27
    • 0025120972 scopus 로고
    • It should be pointed out that this is the only example of a stable, saturated 1,2-dithietane ring system
    • K. C. Nicolaou, C.-K. Hwang, M. E. Duggan and P. J. Carroll, J. Am. Chem. Soc., 109, 3801 (1987); K. C. Nicolaou, C.-K. Hwang, S. DeFrees and N. Stylianides, J. Am. Chem. Soc., 110, 4868 (1988); K. C. Nicolaou, S. A. DeFrees, C.-K. Hwang, N. Stylianides, P. J. Carroll and J. P. Snyder, J. Am. Chem. Soc., 112, 3029 (1990). It should be pointed out that this is the only example of a stable, saturated 1,2-dithietane ring system.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 3029
    • Nicolaou, K.C.1    DeFrees, S.A.2    Hwang, C.-K.3    Stylianides, N.4    Carroll, P.J.5    Snyder, J.P.6
  • 32
    • 0001070462 scopus 로고
    • d) M. Kustos and R. Steudel, J. Org. Chem., 60, 8056 (1995). There are many other molecules which readily lose sulfur; for a summary see C. R. Williams and D. N. Harpp, Sulfur Reports, 10, 103 (1990). In this article there are several systems where the formation of diatomic sulfur is indicated but was not authenticated by appropriate trapping experiments; see references section, p. 167.
    • (1995) J. Org. Chem. , vol.60 , pp. 8056
    • Kustos, M.1    Steudel, R.2
  • 33
    • 84930561161 scopus 로고
    • In this article there are several systems where the formation of diatomic sulfur is indicated but was not authenticated by appropriate trapping experiments; see references section, p. 167
    • d) M. Kustos and R. Steudel, J. Org. Chem., 60, 8056 (1995). There are many other molecules which readily lose sulfur; for a summary see C. R. Williams and D. N. Harpp, Sulfur Reports, 10, 103 (1990). In this article there are several systems where the formation of diatomic sulfur is indicated but was not authenticated by appropriate trapping experiments; see references section, p. 167.
    • (1990) Sulfur Reports , vol.10 , pp. 103
    • Williams, C.R.1    Harpp, D.N.2
  • 34
    • 37049087505 scopus 로고
    • while cyclic tetrasulfide 17b was not mentioned in the article, it has been shown to be in the reaction mixture, T. L. Gilchrist, private communication
    • T. L. Gilchrist and J. E. Wood, J. Chem. Soc., Chem. Commun., 1460 (1992); while cyclic tetrasulfide 17b was not mentioned in the article, it has been shown to be in the reaction mixture, T. L. Gilchrist, private communication.
    • (1992) J. Chem. Soc., Chem. Commun. , pp. 1460
    • Gilchrist, T.L.1    Wood, J.E.2
  • 39
    • 0001715885 scopus 로고
    • evidence for dithietanes is circumstantial. For the preparation of thiosulfenyl chloride 22 and related derivatives, see c) C. R. Williams, J. F. Britten and D. N. Harpp, J. Org. Chem., 59, 806 (1994).
    • (1994) J. Org. Chem. , vol.59 , pp. 806
    • Williams, C.R.1    Britten, J.F.2    Harpp, D.N.3
  • 43
    • 0000710587 scopus 로고
    • b) Of considerable note is the recent, careful work of Steudel on the simplest alkoxy disulfide (dimethoxydisulfane); the gas-phase structure has been determined by electron diffraction; see R. Steudel, H. Schmidt, E. Baumeister, H. Oberhammer and T. Koritsanszky, J. Phys. Chem., 99, 8987 (1995);
    • (1995) J. Phys. Chem. , vol.99 , pp. 8987
    • Steudel, R.1    Schmidt, H.2    Baumeister, E.3    Oberhammer, H.4    Koritsanszky, T.5
  • 45
    • 0011790424 scopus 로고
    • d) Some of the nucleophilic substitution chemistry of alkoxy disulfides has been reported; J. Kagami and S. Motoki, J. Org. Chem., 42, 4139 (1977); A recent paper outlined the photolysis behavior of alkoxy disulfides and their addition to fullerenes; R. Borghi, L. Lunazzi, G. Placucci, G. Cerioni and A. Plumitallo, J. Org. Chem., 61, 3327 (1996).
    • (1977) J. Org. Chem. , vol.42 , pp. 4139
    • Kagami, J.1    Motoki, S.2
  • 46
    • 0000658069 scopus 로고    scopus 로고
    • d) Some of the nucleophilic substitution chemistry of alkoxy disulfides has been reported; J. Kagami and S. Motoki, J. Org. Chem., 42, 4139 (1977); A recent paper outlined the photolysis behavior of alkoxy disulfides and their addition to fullerenes; R. Borghi, L. Lunazzi, G. Placucci, G. Cerioni and A. Plumitallo, J. Org. Chem., 61, 3327 (1996).
    • (1996) J. Org. Chem. , vol.61 , pp. 3327
    • Borghi, R.1    Lunazzi, L.2    Placucci, G.3    Cerioni, G.4    Plumitallo, A.5
  • 47
    • 0003719612 scopus 로고
    • Academic Press, San Diego, CA
    • It should be clarified that in virtually all reactions where diatomic sulfur is transferred, moderate amounts of tetrasulfide adduct 17a,b are isolated. This tetrasulfide can be treated with triphenylphosphine and converted back to the disulfide adduct 16a,b in a nearly quantitative fashion. See reference 23 for details. This transformation of a diene to a cyclic disulfide represents a useful addition to the arsenal of heteroatoms in Diels-Alder synthesis; see, D. L. Boger and S. N. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, CA, 1987. In addition, we have found that consistent results are obtained when MgO is added to the reaction mixture. Apparently this ensures that there are no acid traces in the alkoxy disulfides 24. It has been shown that 24 decomposes in the presence of Lewis acids to sulfites, sulfinates and elemental sulfur; see M. Kobayashi H. Minato and K. Shimada, Int. J. Sulfur Chem., 1, 105 (1971). We have confirmed this result.
    • (1987) Hetero Diels-Alder Methodology in Organic Synthesis
    • Boger, D.L.1    Weinreb, S.N.2
  • 48
    • 3242671172 scopus 로고
    • We have confirmed this result
    • It should be clarified that in virtually all reactions where diatomic sulfur is transferred, moderate amounts of tetrasulfide adduct 17a,b are isolated. This tetrasulfide can be treated with triphenylphosphine and converted back to the disulfide adduct 16a,b in a nearly quantitative fashion. See reference 23 for details. This transformation of a diene to a cyclic disulfide represents a useful addition to the arsenal of heteroatoms in Diels-Alder synthesis; see, D. L. Boger and S. N. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, CA, 1987. In addition, we have found that consistent results are obtained when MgO is added to the reaction mixture. Apparently this ensures that there are no acid traces in the alkoxy disulfides 24. It has been shown that 24 decomposes in the presence of Lewis acids to sulfites, sulfinates and elemental sulfur; see M. Kobayashi H. Minato and K. Shimada, Int. J. Sulfur Chem., 1, 105 (1971). We have confirmed this result.
    • (1971) Int. J. Sulfur Chem. , vol.1 , pp. 105
    • Kobayashi, M.1    Minato, H.2    Shimada, K.3
  • 50
    • 84963177623 scopus 로고
    • b) K. Steliou, Y. Gareau, G. Milot and P. Salama, Phosphorus, Sulfur and Silica, 43, 209 (1989); another paper by Steliou addresses the issue of diatomic sulfur as a free species; see K. Steliou, P. Salama and X. Yu, J. Am. Chem. Soc., 114, 1456 (1992).
    • (1989) Phosphorus, Sulfur and Silica , vol.43 , pp. 209
    • Steliou, K.1    Gareau, Y.2    Milot, G.3    Salama, P.4
  • 51
    • 0000175158 scopus 로고
    • b) K. Steliou, Y. Gareau, G. Milot and P. Salama, Phosphorus, Sulfur and Silica, 43, 209 (1989); another paper by Steliou addresses the issue of diatomic sulfur as a free species; see K. Steliou, P. Salama and X. Yu, J. Am. Chem. Soc., 114, 1456 (1992).
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1456
    • Steliou, K.1    Salama, P.2    Yu, X.3
  • 54
    • 58149503355 scopus 로고
    • N. L. Allinger, M. J. Hickey and J. Kao, J. Am. Chem. Soc., 98, 2741 (1976); O. Foss, Adv. Inorg. Chem. Radiochem., 2, 237 (1960).
    • (1960) Adv. Inorg. Chem. Radiochem. , vol.2 , pp. 237
    • Foss, O.1
  • 57
    • 84945071330 scopus 로고
    • F. Seel and R. Budenz, Chem. Ber., 98, 251 (1965); R. D. Brown, F. R. Burden and G. P. Pez, J. Chem. Soc., Chem. Commun. 277 (1965); W. Gombler, J. Schaebs and H. Willner, Inorg. Chem., 29, 2697 (1990); R. W. Davis and S. Firth, J. Mol Spectrosc., 145, 225 (1991).
    • (1965) Chem. Ber. , vol.98 , pp. 251
    • Seel, F.1    Budenz, R.2
  • 58
    • 37049043846 scopus 로고
    • F. Seel and R. Budenz, Chem. Ber., 98, 251 (1965); R. D. Brown, F. R. Burden and G. P. Pez, J. Chem. Soc., Chem. Commun. 277 (1965); W. Gombler, J. Schaebs and H. Willner, Inorg. Chem., 29, 2697 (1990); R. W. Davis and S. Firth, J. Mol Spectrosc., 145, 225 (1991).
    • (1965) J. Chem. Soc., Chem. Commun. , pp. 277
    • Brown, R.D.1    Burden, F.R.2    Pez, G.P.3
  • 59
    • 0001021057 scopus 로고
    • F. Seel and R. Budenz, Chem. Ber., 98, 251 (1965); R. D. Brown, F. R. Burden and G. P. Pez, J. Chem. Soc., Chem. Commun. 277 (1965); W. Gombler, J. Schaebs and H. Willner, Inorg. Chem., 29, 2697 (1990); R. W. Davis and S. Firth, J. Mol Spectrosc., 145, 225 (1991).
    • (1990) Inorg. Chem. , vol.29 , pp. 2697
    • Gombler, W.1    Schaebs, J.2    Willner, H.3
  • 60
    • 0041020124 scopus 로고
    • F. Seel and R. Budenz, Chem. Ber., 98, 251 (1965); R. D. Brown, F. R. Burden and G. P. Pez, J. Chem. Soc., Chem. Commun. 277 (1965); W. Gombler, J. Schaebs and H. Willner, Inorg. Chem., 29, 2697 (1990); R. W. Davis and S. Firth, J. Mol Spectrosc., 145, 225 (1991).
    • (1991) J. Mol Spectrosc. , vol.145 , pp. 225
    • Davis, R.W.1    Firth, S.2
  • 61
    • 33847088730 scopus 로고    scopus 로고
    • B. Solouki and H. Bock, Inorg. Chem., 16, 665 (1977); our own work on this aspect shows a barrier of 36.7 kcal/mol at the MP2/6-31 + G* level, J. P. Snyder and D. N. Harpp, unpublished results.
    • (1977) Inorg. Chem. , vol.16 , pp. 665
    • Solouki, B.1    Bock, H.2
  • 62
    • 33847088730 scopus 로고    scopus 로고
    • unpublished results
    • B. Solouki and H. Bock, Inorg. Chem., 16, 665 (1977); our own work on this aspect shows a barrier of 36.7 kcal/mol at the MP2/6-31 + G* level, J. P. Snyder and D. N. Harpp, unpublished results.
    • Snyder, J.P.1    Harpp, D.N.2
  • 63
    • 0007869418 scopus 로고
    • B. M. Chadwick, J. M. Grzybowski and D. A. Long, J. Mol. Struct. 48, 139 (1978); M. Feuerhahn and G. Vahl, Chem. Phys. Lett., 65, 322 (1979); D. Martinez, Z. Chem., 20, 332 (1980); G. Holzmann, M. Feuerhahn, R. Minkwitz and G. Vahl, J. Chem. Res. Synop., 71 (1980).
    • (1978) J. Mol. Struct. , vol.48 , pp. 139
    • Chadwick, B.M.1    Grzybowski, J.M.2    Long, D.A.3
  • 64
    • 0007816494 scopus 로고
    • B. M. Chadwick, J. M. Grzybowski and D. A. Long, J. Mol. Struct. 48, 139 (1978); M. Feuerhahn and G. Vahl, Chem. Phys. Lett., 65, 322 (1979); D. Martinez, Z. Chem., 20, 332 (1980); G. Holzmann, M. Feuerhahn, R. Minkwitz and G. Vahl, J. Chem. Res. Synop., 71 (1980).
    • (1979) Chem. Phys. Lett. , vol.65 , pp. 322
    • Feuerhahn, M.1    Vahl, G.2
  • 65
    • 84983966666 scopus 로고
    • B. M. Chadwick, J. M. Grzybowski and D. A. Long, J. Mol. Struct. 48, 139 (1978); M. Feuerhahn and G. Vahl, Chem. Phys. Lett., 65, 322 (1979); D. Martinez, Z. Chem., 20, 332 (1980); G. Holzmann, M. Feuerhahn, R. Minkwitz and G. Vahl, J. Chem. Res. Synop., 71 (1980).
    • (1980) Z. Chem. , vol.20 , pp. 332
    • Martinez, D.1
  • 66
    • 0007869418 scopus 로고
    • B. M. Chadwick, J. M. Grzybowski and D. A. Long, J. Mol. Struct. 48, 139 (1978); M. Feuerhahn and G. Vahl, Chem. Phys. Lett., 65, 322 (1979); D. Martinez, Z. Chem., 20, 332 (1980); G. Holzmann, M. Feuerhahn, R. Minkwitz and G. Vahl, J. Chem. Res. Synop., 71 (1980).
    • (1980) J. Chem. Res. Synop. , vol.71
    • Holzmann, G.1    Feuerhahn, M.2    Minkwitz, R.3    Vahl, G.4
  • 67
    • 0039833449 scopus 로고
    • it should be noted that these compounds are unstable over time
    • Q. E. Thompson, M. M. Crutchfield and M. W. Dietrich, J. Org. Chem., 30, 2696 (1965); it should be noted that these compounds are unstable over time.
    • (1965) J. Org. Chem. , vol.30 , pp. 2696
    • Thompson, Q.E.1    Crutchfield, M.M.2    Dietrich, M.W.3
  • 72
    • 0343733208 scopus 로고
    • Elsevier Press, Amsterdam, B. Zwanenburg and J. J. H. Klunder, Ed.
    • d) In addition, MINDO/3 calculations carried out in our laboratory using the atoms Cl, O and H, clearly indicate the same trend, see D. N. Harpp in Perspectives in The Organic Chemistry of Sulfur, Elsevier Press, Amsterdam, B. Zwanenburg and J. J. H. Klunder, Ed., p. 1, 1986; in addition, calculations at the MP2/6-31 + G* level show the same trend, J. P. Snyder and D. N. Harpp, unpublished results;
    • (1986) Perspectives in The Organic Chemistry of Sulfur , pp. 1
    • Harpp, D.N.1
  • 73
    • 0041020120 scopus 로고    scopus 로고
    • unpublished results
    • d) In addition, MINDO/3 calculations carried out in our laboratory using the atoms Cl, O and H, clearly indicate the same trend, see D. N. Harpp in Perspectives in The Organic Chemistry of Sulfur, Elsevier Press, Amsterdam, B. Zwanenburg and J. J. H. Klunder, Ed., p. 1, 1986; in addition, calculations at the MP2/6-31 + G* level show the same trend, J. P. Snyder and D. N. Harpp, unpublished results;
    • Snyder, J.P.1    Harpp, D.N.2
  • 74
    • 33845553498 scopus 로고
    • e) For a lengthy review on the subject of branch-bonding in sulfur compounds, see G. W. Kutney and K. Turnbull, Chem. Rev., 82, 333 (1982).
    • (1982) Chem. Rev. , vol.82 , pp. 333
    • Kutney, G.W.1    Turnbull, K.2
  • 75
  • 76
    • 0000259044 scopus 로고
    • Typical S-S bond rotational barriers for aliphatic disulfides are in the range of 2-16 kcal/mol with the most typical values being ca. 9 kcal/mol; R. R. Fraser, G. Boussard, J. K. Saunders, J. B. Lambert, J. Am. Chem. Soc., 93, 3822 (1971).
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 3822
    • Fraser, R.R.1    Boussard, G.2    Saunders, J.K.3    Lambert, J.B.4
  • 79
    • 0039241726 scopus 로고    scopus 로고
    • St. John's, Newfoundland, Canada, June
    • A. Rys, A. G. Shaver and D. N. Harpp, 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; it should be pointed out that when DMSO is used in such reactions, a small amount of the DMSO disproportionates into dimethylsulfone and dimethylsulfide; see V. J. Traynelis and W. L. Hergenrother, J. Org. Chem., 29, 221 (1963); D. L. Head and C. G. McCarty, Tetrahedron Lett., 1405 (1973).
    • (1996) 79th Canadian Chemical Conference
    • Rys, A.1    Shaver, A.G.2    Harpp, D.N.3
  • 80
    • 0342306341 scopus 로고
    • A. Rys, A. G. Shaver and D. N. Harpp, 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; it should be pointed out that when DMSO is used in such reactions, a small amount of the DMSO disproportionates into dimethylsulfone and dimethylsulfide; see V. J. Traynelis and W. L. Hergenrother, J. Org. Chem., 29, 221 (1963); D. L. Head and C. G. McCarty, Tetrahedron Lett., 1405 (1973).
    • (1963) J. Org. Chem. , vol.29 , pp. 221
    • Traynelis, V.J.1    Hergenrother, W.L.2
  • 81
    • 0010663862 scopus 로고
    • A. Rys, A. G. Shaver and D. N. Harpp, 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; it should be pointed out that when DMSO is used in such reactions, a small amount of the DMSO disproportionates into dimethylsulfone and dimethylsulfide; see V. J. Traynelis and W. L. Hergenrother, J. Org. Chem., 29, 221 (1963); D. L. Head and C. G. McCarty, Tetrahedron Lett., 1405 (1973).
    • (1973) Tetrahedron Lett. , pp. 1405
    • Head, D.L.1    McCarty, C.G.2
  • 83
    • 0009409420 scopus 로고    scopus 로고
    • and references cited therein
    • In many of the sulfur-incorporation reactions in the literature, sulfur is "activated" by the addition of a base or ammonia; for comments on the vulcanization of rubber see S. Oae, Main Group Chemistry News, 4, 10 (1996) and references cited therein; also see U. Chiacchio, A. Corsaro, A. Rescifina, M. G. Testa and G. Purrello, Heterocycles, 36, 223, 1993.
    • (1996) Main Group Chemistry News , vol.4 , pp. 10
    • Oae, S.1
  • 84
    • 0009409420 scopus 로고    scopus 로고
    • In many of the sulfur-incorporation reactions in the literature, sulfur is "activated" by the addition of a base or ammonia; for comments on the vulcanization of rubber see S. Oae, Main Group Chemistry News, 4, 10 (1996) and references cited therein; also see U. Chiacchio, A. Corsaro, A. Rescifina, M. G. Testa and G. Purrello, Heterocycles, 36, 223, 1993.
    • (1993) Heterocycles , vol.36 , pp. 223
    • Chiacchio, U.1    Corsaro, A.2    Rescifina, A.3    Testa, M.G.4    Purrello, G.5
  • 86
    • 0027405334 scopus 로고
    • B. C. Fulcher, M. L. Hinter and M. L. Welker, Synth. Commun., 23, 217 (1993). An example of sulfur transfer to dienes, involving what is sometimes called "activated sulfur", is found in the reaction of elemental sulfur with myrcene [2-(4-methyl-3-pentenyl)-1,3-butadiene)] as a conjugated diene trap; here, the solvent is DMF and pyridine is added as "catalyst". In this case the yield of cyclic disulfide is relatively low (30%) and there were several other sulfurated products noted; see J. A. Elvidge, S. P. Jones and T. L. Peppard, J. Chem. Soc., Perkin I, 1089 (1983). In addition, when myrcene is treated with sulfur and UV light, a very low yield of sulfurated products result. A recent report has shown a relatively facile introduction of a two-sulfur unit (by way of elemental sulfur in a polar solvent (acetonitrile)) into strained, cyclic thioether; D. A. Nugiel and M. M. Abelman, J. Org. Chem., 60, 3554 (1995).
    • (1993) Synth. Commun. , vol.23 , pp. 217
    • Fulcher, B.C.1    Hinter, M.L.2    Welker, M.L.3
  • 87
    • 37049110980 scopus 로고
    • B. C. Fulcher, M. L. Hinter and M. L. Welker, Synth. Commun., 23, 217 (1993). An example of sulfur transfer to dienes, involving what is sometimes called "activated sulfur", is found in the reaction of elemental sulfur with myrcene [2-(4-methyl-3-pentenyl)-1,3-butadiene)] as a conjugated diene trap; here, the solvent is DMF and pyridine is added as "catalyst". In this case the yield of cyclic disulfide is relatively low (30%) and there were several other sulfurated products noted; see J. A. Elvidge, S. P. Jones and T. L. Peppard, J. Chem. Soc., Perkin I, 1089 (1983). In addition, when myrcene is treated with sulfur and UV light, a very low yield of sulfurated products result. A recent report has shown a relatively facile introduction of a two-sulfur unit (by way of elemental sulfur in a polar solvent (acetonitrile)) into strained, cyclic thioether; D. A. Nugiel and M. M. Abelman, J. Org. Chem., 60, 3554 (1995).
    • (1983) J. Chem. Soc., Perkin I , pp. 1089
    • Elvidge, J.A.1    Jones, S.P.2    Peppard, T.L.3
  • 88
    • 0007004411 scopus 로고
    • B. C. Fulcher, M. L. Hinter and M. L. Welker, Synth. Commun., 23, 217 (1993). An example of sulfur transfer to dienes, involving what is sometimes called "activated sulfur", is found in the reaction of elemental sulfur with myrcene [2-(4-methyl-3-pentenyl)-1,3-butadiene)] as a conjugated diene trap; here, the solvent is DMF and pyridine is added as "catalyst". In this case the yield of cyclic disulfide is relatively low (30%) and there were several other sulfurated products noted; see J. A. Elvidge, S. P. Jones and T. L. Peppard, J. Chem. Soc., Perkin I, 1089 (1983). In addition, when myrcene is treated with sulfur and UV light, a very low yield of sulfurated products result. A recent report has shown a relatively facile introduction of a two-sulfur unit (by way of elemental sulfur in a polar solvent (acetonitrile)) into strained, cyclic thioether; D. A. Nugiel and M. M. Abelman, J. Org. Chem., 60, 3554 (1995).
    • (1995) J. Org. Chem. , vol.60 , pp. 3554
    • Nugiel, D.A.1    Abelman, M.M.2
  • 90
    • 0040426021 scopus 로고    scopus 로고
    • Sulfur monoxide can be generated by reduction of sulfur dioxide with sulfur vapor; like oxygen, it has a triplet ground state; see ref. 1
    • Sulfur monoxide can be generated by reduction of sulfur dioxide with sulfur vapor; like oxygen, it has a triplet ground state; see ref. 1.
  • 91
    • 0343298038 scopus 로고    scopus 로고
    • in press
    • I. A. Abu-Yousef and D. N. Harpp, Sulfur Reports, 0000, 1996, in press. The photoelectron spectrum has been reported, see J. M. Dyke, A. Morris and I. R. Trickle, J. Chem. Soc., Faraday Trans., 70, 1818 (1974).
    • (1996) Sulfur Reports
    • Abu-Yousef, I.A.1    Harpp, D.N.2
  • 92
  • 93
    • 0001548562 scopus 로고
    • G. E. Hartzell and J. N. Paige, J. Am. Chem. Soc., 88, 2616 (1966); G. E. Hartzell and J. N. Paige, J. Org. Chem., 32, 459 (1967); sulfur monoxide is harsh, causing burns.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 2616
    • Hartzell, G.E.1    Paige, J.N.2
  • 94
    • 0007618085 scopus 로고
    • sulfur monoxide is harsh, causing burns
    • G. E. Hartzell and J. N. Paige, J. Am. Chem. Soc., 88, 2616 (1966); G. E. Hartzell and J. N. Paige, J. Org. Chem., 32, 459 (1967); sulfur monoxide is harsh, causing burns.
    • (1967) J. Org. Chem. , vol.32 , pp. 459
    • Hartzell, G.E.1    Paige, J.N.2
  • 95
    • 33947473240 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 2986
    • Cotton, R.A.1    Francis, F.2
  • 96
    • 0039241709 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1962) J. Org. Chem. , vol.27 , pp. 4353
    • Topping, R.M.1    Kharasch, N.2
  • 97
    • 0011673394 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 212
    • Kochi, J.K.1
  • 98
    • 33847087812 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1968) J. Phys. Chem. , vol.84 , pp. 3024
    • Dorer, F.H.1    Salomon, K.E.2
  • 99
    • 0039241720 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1969) Tetrahedron Lett. , pp. 2743
    • Kondo, K.1    Negishi, A.2    Tsuchihashi, G.3
  • 100
    • 33947473240 scopus 로고
    • R. A. Cotton and F. Francis, J. Am. Chem. Soc., 82, 2986 (1960); R. M. Topping and N. Kharasch, J. Org. Chem., 27, 4353 (1962); J. K. Kochi, J. Am. Chem. Soc., 84, 212 (1962); F. H. Dorer and K. E. Salomon, J. Phys. Chem., 84, 3024 (1968); K. Kondo, A. Negishi and G. Tsuchihashi, Tetrahedron Lett., 2743 (1969); O. Heyke, A. Neher and L.-P. Lorenz., Z. anorg. allg. Chem., 23, 608 (1992).
    • (1992) Z. Anorg. Allg. Chem. , vol.23 , pp. 608
    • Heyke, O.1    Neher, A.2    Lorenz, L.-P.3
  • 101
    • 85023248288 scopus 로고
    • R. M. Dodson and J. P. Nelson, J. Chem. Soc., Chem. Commun., 1159 (1967); R. M. Dodson and F. R. Sauers, ibid., 1189 (1967); Y. L. Chow, J. N. S. Tam and J. E. Blier, ibid., 1604 (1970); A. G. Anastassiou and B. Y. H. Chao, ibid, 979 (1971).
    • (1967) J. Chem. Soc., Chem. Commun. , pp. 1159
    • Dodson, R.M.1    Nelson, J.P.2
  • 102
    • 30944456973 scopus 로고
    • R. M. Dodson and J. P. Nelson, J. Chem. Soc., Chem. Commun., 1159 (1967); R. M. Dodson and F. R. Sauers, ibid., 1189 (1967); Y. L. Chow, J. N. S. Tam and J. E. Blier, ibid., 1604 (1970); A. G. Anastassiou and B. Y. H. Chao, ibid, 979 (1971).
    • (1967) J. Chem. Soc., Chem. Commun. , pp. 1189
    • Dodson, R.M.1    Sauers, F.R.2
  • 103
    • 37049139685 scopus 로고
    • R. M. Dodson and J. P. Nelson, J. Chem. Soc., Chem. Commun., 1159 (1967); R. M. Dodson and F. R. Sauers, ibid., 1189 (1967); Y. L. Chow, J. N. S. Tam and J. E. Blier, ibid., 1604 (1970); A. G. Anastassiou and B. Y. H. Chao, ibid, 979 (1971).
    • (1970) J. Chem. Soc., Chem. Commun. , pp. 1604
    • Chow, Y.L.1    Tam, J.N.S.2    Blier, J.E.3
  • 104
    • 0002957031 scopus 로고
    • R. M. Dodson and J. P. Nelson, J. Chem. Soc., Chem. Commun., 1159 (1967); R. M. Dodson and F. R. Sauers, ibid., 1189 (1967); Y. L. Chow, J. N. S. Tam and J. E. Blier, ibid., 1604 (1970); A. G. Anastassiou and B. Y. H. Chao, ibid, 979 (1971).
    • (1971) J. Chem. Soc., Chem. Commun. , pp. 979
    • Anastassiou, A.G.1    Chao, B.Y.H.2
  • 106
    • 0039241698 scopus 로고    scopus 로고
    • P. Chao and D. M. Lemal, J. Am. Chem. Soc., 95, 920 (1973); ibid., 922.
    • J. Am. Chem. Soc. , pp. 922
  • 112
    • 0039241697 scopus 로고    scopus 로고
    • manuscript submitted
    • I. A. Abu-Yousef and D. N. Harpp, 78th Canadian Chemical Conference, Guelph, Ontario, Canada, June, 1995; I. A. Abu-Yousef and D. N. Harpp, manuscript submitted.
    • Abu-Yousef, I.A.1    Harpp, D.N.2
  • 114
    • 0039833404 scopus 로고    scopus 로고
    • Emory University, private communication
    • J. P. Snyder, Emory University, private communication.
    • Snyder, J.P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.