Peroxides of Sterically Hindered Derivatives of Schlenk Hydrocarbon Diradical

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6524-6528

  Rajca, Andrzej ^a   Rajca, Suchada ^a   Desai, Shailesh R ^a   Day, Victor W ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000955835     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961879x     Document Type: Article

References (40)

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21. Stark and co-workers reported their apparently unsuccessful attempts to obtain exocyclic tetraphenyl-substituted m-xylylene and its products of reaction with oxygen: Stark, O.; Garben, O. Ber. Dtsch. Chem. Ges. 1913, 46, 659, 2252. Stark, O.; Garben, O.; Klebahn, L. Ber. Dtsch. Chem. Ges. 1913, 46, 2542. Stark, O.; Klebahn, L. Ber. Dtsch. Chem. Ges. 1914, 47, 125.
22. Stark and co-workers reported their apparently unsuccessful attempts to obtain exocyclic tetraphenyl-substituted m-xylylene and its products of reaction with oxygen: Stark, O.; Garben, O. Ber. Dtsch. Chem. Ges. 1913, 46, 659, 2252. Stark, O.; Garben, O.; Klebahn, L. Ber. Dtsch. Chem. Ges. 1913, 46, 2542. Stark, O.; Klebahn, L. Ber. Dtsch. Chem. Ges. 1914, 47, 125.
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30. For an overview of calculations of NMR chemical shifts, with proteins as examples, see: Augspurger, J. D.; Dykstra, C. E. Prog. NMR Spectrosc. 1995, 30, 1. Ring current contribution: Haigh, C. W.; Mallion, R. B. Prog. NMR Spectrosc. 1980, 13, 303. Haigh, C. W.; Mallion, R. B. Org. Magn. Reson. 1972, 4, 203.
31. For an overview of calculations of NMR chemical shifts, with proteins as examples, see: Augspurger, J. D.; Dykstra, C. E. Prog. NMR Spectrosc. 1995, 30, 1. Ring current contribution: Haigh, C. W.; Mallion, R. B. Prog. NMR Spectrosc. 1980, 13, 303. Haigh, C. W.; Mallion, R. B. Org. Magn. Reson. 1972, 4, 203.
32. For an overview of calculations of NMR chemical shifts, with proteins as examples, see: Augspurger, J. D.; Dykstra, C. E. Prog. NMR Spectrosc. 1995, 30, 1. Ring current contribution: Haigh, C. W.; Mallion, R. B. Prog. NMR Spectrosc. 1980, 13, 303. Haigh, C. W.; Mallion, R. B. Org. Magn. Reson. 1972, 4, 203.
33. 2: Mustafa, A. J. Chem. Soc. 1952, 2435.
34. Rajca, S.; Rajca, A. J. Am. Chem. Soc. 1995, 117, 9172.
35. Two propeller diastereomers could be isolated for the exceedingly hindered perchlorocarbon derivative of the Schlenk hydrocarbon (ref 5).
36. Whether spin multiplicity will have a significant direct effect on reactivity of 3 toward oxygen is not clear. Recent reports indicate that the rates for the reaction with oxygen are only slightly lower for singlet state diradicals, compared to many triplet state diradicals (with different structures), e.g., Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073. Heath, R. B.; Bush, L. C.; Feng, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. Furthermore, oxygen and other paramagnetic molecules are known to catalyze intersystem crossing, e.g., Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995; pp. 254-256. In organometallics, intersystem crossings are expected to be much faster compared to typical organics, but still the notion of significant effect of spin state on reactivity reemerges only to be disproved: Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745 and references therein.
37. Whether spin multiplicity will have a significant direct effect on reactivity of 3 toward oxygen is not clear. Recent reports indicate that the rates for the reaction with oxygen are only slightly lower for singlet state diradicals, compared to many triplet state diradicals (with different structures), e.g., Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073. Heath, R. B.; Bush, L. C.; Feng, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. Furthermore, oxygen and other paramagnetic molecules are known to catalyze intersystem crossing, e.g., Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995; pp. 254-256. In organometallics, intersystem crossings are expected to be much faster compared to typical organics, but still the notion of significant effect of spin state on reactivity reemerges only to be disproved: Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745 and references therein.
38. Whether spin multiplicity will have a significant direct effect on reactivity of 3 toward oxygen is not clear. Recent reports indicate that the rates for the reaction with oxygen are only slightly lower for singlet state diradicals, compared to many triplet state diradicals (with different structures), e.g., Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073. Heath, R. B.; Bush, L. C.; Feng, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. Furthermore, oxygen and other paramagnetic molecules are known to catalyze intersystem crossing, e.g., Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995; pp. 254-256. In organometallics, intersystem crossings are expected to be much faster compared to typical organics, but still the notion of significant effect of spin state on reactivity reemerges only to be disproved: Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745 and references therein.
39. Whether spin multiplicity will have a significant direct effect on reactivity of 3 toward oxygen is not clear. Recent reports indicate that the rates for the reaction with oxygen are only slightly lower for singlet state diradicals, compared to many triplet state diradicals (with different structures), e.g., Reynolds, J. H.; Berson, J. A.; Kumashiro, K. K.; Duchamp, J. C.; Zilm, K. W.; Scaiano, J. C.; Berinstain, A. B.; Rubello, A.; Vogel, P. J. Am. Chem. Soc. 1993, 115, 8073. Heath, R. B.; Bush, L. C.; Feng, X.-W.; Berson, J. A.; Scaiano, J. C.; Berinstain, A. B. J. Phys. Chem. 1993, 97, 13355. Furthermore, oxygen and other paramagnetic molecules are known to catalyze intersystem crossing, e.g., Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH: New York, 1995; pp. 254-256. In organometallics, intersystem crossings are expected to be much faster compared to typical organics, but still the notion of significant effect of spin state on reactivity reemerges only to be disproved: Detrich, J. L.; Reinaud, O. M.; Rheingold, A. L.; Theopold, K. H. J. Am. Chem. Soc. 1995, 117, 11745 and references therein.
40. 2 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.