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Volumn 65, Issue 6, 2000, Pages 1807-1817

Thermolysis and photosensitized oxygenation of tetrasubstituted cyclopropenes

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; HYDROPEROXIDE; PROPYLENE;

EID: 0034708423     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991803b     Document Type: Article
Times cited : (14)

References (87)
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    • (g) This short-chain polyperoxidation occurs only very slowly at room temperature to ultimately yield 20; see the last entry in Table 2.
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    • See the following leading papers and the references therein: (a) Maynard, G. D.; Paquette, L. A. J. Org. Chem. 1991, 56, 5480-5482. (b) Friedrich, L. E.; Leckonby, R. A.; Stout, D. M. J. Org. Chem. 1980, 45, 3198-3202. (c) Crandall, J. K.; Conover, W. W., II. J. Org. Chem. 1978, 43, 1323-1327. (d) refs 1d and 9.
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    • See the following leading papers and the references therein: (a) Maynard, G. D.; Paquette, L. A. J. Org. Chem. 1991, 56, 5480- 5482. (b) Friedrich, L. E.; Leckonby, R. A.; Stout, D. M. J. Org. Chem. 1980, 45, 3198-3202. (c) Crandall, J. K.; Conover, W. W., II. J. Org. Chem. 1978, 43, 1323-1327. (d) refs 1d and 9.
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    • 26b give a substantially higher value of 3.164 Å. In Scheme 8, we have given the average value of 3.088 Å. (a) Shand, W., Jr.; Schomaker, V.; Fischer, J. F. J. Am. Chem. Soc. 1944, 66, 636-640. See also: Huang, Y. S.; Beaudet, R. A. J. Chem. Phys. 1970, 52, 935-940. (b) Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1294-1301.
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    • 26b give a substantially higher value of 3.164 Å. In Scheme 8, we have given the average value of 3.088 Å. (a) Shand, W., Jr.; Schomaker, V.; Fischer, J. F. J. Am. Chem. Soc. 1944, 66, 636- 640. See also: Huang, Y. S.; Beaudet, R. A. J. Chem. Phys. 1970, 52, 935-940. (b) Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1294-1301.
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    • 26b give a substantially higher value of 3.164 Å. In Scheme 8, we have given the average value of 3.088 Å. (a) Shand, W., Jr.; Schomaker, V.; Fischer, J. F. J. Am. Chem. Soc. 1944, 66, 636- 640. See also: Huang, Y. S.; Beaudet, R. A. J. Chem. Phys. 1970, 52, 935-940. (b) Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1294-1301.
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    • 27b yield a substantially lower value of 3.229 Å. In Scheme 8, we have cited the experimental value of 3.241 Å. (a) Kemp, M. K.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 3163-3167. See also: Allen, F. A. Tetrahedron 1982, 38, 645-655. (b) Eckert- Makasic, M.; Makasic, Z. B. J. Mol. Struct., THEOCHEM 1982, 86, 325-340.
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    • 27b yield a substantially lower value of 3.229 Å. In Scheme 8, we have cited the experimental value of 3.241 Å. (a) Kemp, M. K.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 3163-3167. See also: Allen, F. A. Tetrahedron 1982, 38, 645-655. (b) Eckert- Makasic, M.; Makasic, Z. B. J. Mol. Struct., THEOCHEM 1982, 86, 325-340.
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    • 27b yield a substantially lower value of 3.229 Å. In Scheme 8, we have cited the experimental value of 3.241 Å. (a) Kemp, M. K.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 3163-3167. See also: Allen, F. A. Tetrahedron 1982, 38, 645-655. (b) Eckert-Makasic, M.; Makasic, Z. B. J. Mol. Struct., THEOCHEM 1982, 86, 325-340.
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    • Reference 6b, Table 2, pp 291-295 and 298ff
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    • note
    • 29e-h primarily because ionization potential is by no means the sole determinant of reaction rate.
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    • 13 ft × 1/4 in. copper column packed with 20% Carbowax 20M Chromosorb WAW
    • (a) 13 ft × 1/4 in. copper column packed with 20% Carbowax 20M Chromosorb WAW.
  • 87
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    • 13 ft × 1/4 in. copper column packed with 7% SE-30 on Chromosorb WAW
    • (b) 13 ft × 1/4 in. copper column packed with 7% SE-30 on Chromosorb WAW.


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