-
2
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0004098344
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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);
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The Chemical and Engineering News
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6
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0029891376
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2) complex at very low temperature; see G. D. Brabson, A. Citra, L. Andres, R. D. Davy and M. Neurock; J. Am. Chem. Soc., 118, 5469 (1996).
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B. Meyer, Ed., Interscience, New York
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R. F. Barrow and R. P. Duparcq, in Elemental Sulfur, B. Meyer, Ed., Interscience, New York, 1965.
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9
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K. S. Noll, M. A. McGrath, L. M. Trafton, S. K. Atreya, J. J. Caldwell, H. A. Weaver, R. V. Yelle, C. Barnet and S. Edgington, Science, 267, 1307 (1995).
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10
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Washington, DC, October 24
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The Washington Post, Washington, DC, October 24, 1994 p A3.
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The Washington Post
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12
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0041020138
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Ph.D. thesis, University of Arizona, Professor Richard Glass, supervisor, University Microfilms, Ann Arbor, MI, 77-11, 451
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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.
-
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Smith, D.L.1
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13
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0000736856
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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).
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Steliou, K.1
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14
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0001619246
-
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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).
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Matturro, M.G.1
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15
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2042437127
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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).
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Steliou, K.1
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16
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0000877306
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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).
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Orahovatiz, A.1
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17
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-
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).
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J. Org. Chem.
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Bishop, J.E.1
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K. Steliou, P. Salama, D. Brodeur and Y. Gareau, J. Am. Chem. Soc., 109, 926 (1987).
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Steliou, K.1
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20
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0012182803
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2S, see H. Bender, F. Carnovale, J. B. Peel and C. Wentrup, J. Am. Chem. Soc., 110, 3458 (1988).
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0040426052
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2S, see H. Bender, F. Carnovale, J. B. Peel and C. Wentrup, J. Am. Chem. Soc., 110, 3458 (1988).
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22
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0001284193
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2S, see H. Bender, F. Carnovale, J. B. Peel and C. Wentrup, J. Am. Chem. Soc., 110, 3458 (1988).
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Tetrahedron Lett.
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Ando, W.1
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23
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0024012595
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2S, see H. Bender, F. Carnovale, J. B. Peel and C. Wentrup, J. Am. Chem. Soc., 110, 3458 (1988).
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Bender, H.1
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25
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0001267833
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-
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.
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J. Am. Chem. Soc.
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Nicolaou, K.C.1
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26
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33845278183
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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.
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Nicolaou, K.C.1
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0025120972
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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.
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a) B. L. Chenard, R. L. Harlow. A. L. Johnson and S. A. Vladerchick, J. Am. Chem. Soc., 107, 3871 (1985);
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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.
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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
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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.
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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
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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.
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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).
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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);
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in addition, the crystal structure has been carried out at 110 °K, see: c) T. Koritsanszky, J. Buschmann, P. Luger, H. Schmidt and R. Steudel, J. Phys. Chem., 96, 9243, (1994);
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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).
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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).
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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.
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Boger, D.L.1
Weinreb, S.N.2
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We have confirmed this result
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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.
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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).
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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.
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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;
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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;
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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).
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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).
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and references cited therein
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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.
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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).
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Sulfur monoxide can be generated by reduction of sulfur dioxide with sulfur vapor; like oxygen, it has a triplet ground state; see ref. 1.
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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).
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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.
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