Synthesis of cyclic peroxides by chemo- and regioselective peroxidation of dienes with Co(II)/O2/Et3SiH

Journal of Organic Chemistry

Volumn 70, Issue 1, 2005, Pages 251-260

  Tokuyasu, Takahiro ^a   Kunikawa, Shigeki ^a   McCullough, Kevin J ^b   Masuyama, Araki ^a   Nojima, Masatomo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COBALT COMPOUNDS; DERIVATIVES; PEROXIDES;

ALKENE SUBSTRATES; DIENE STRUCTURES; REGIOSELECTIVITY; RELATIVE REACTIONS;

OLEFINS;

(4,4,5 TRIMETHYL 5 PHENYL 1,2 DIOXOLAN 3 YL)METHYL HYDROPEROXIDE; 1 (5,6 DIMETHYL 6 PHENYL 1,2 DIOXAN 3 YL)PROPAN 2 YL HYDROPEROXIDE; 1,3 DIOXOLANE DERIVATIVE; 2 (5,5,6 TRIMETHYL 6 PHENYL 1,2 DIOXAN 3 YL)PROPAN 2 YL HYDROPEROXIDE; 2 (6 METHYL 5,6 DIPHENYL 1,2 DIOXAN 3 YL)PROPAN 2 YL HYDROPEROXIDE; 2 (6 METHYL 6 PHENYL 1,2 DIOXAN 3 YL)PROPAN 2 YL HYDROPEROXIDE; 2 (TETRAHYDRO 4,4 DIMETHYLFURAN 3 YL)PROPAN 2 YL HYDROPEROXIDE; 2 METHYL 1 PHENYLPROPAN 2 YL HYDROPEROXIDE; 2 METHYL 5 PHENYL 5 HEXEN 2 YL HYDROPEROXIDE; 3,3 DIMETHYL 2 PHENYLBUTAN 2 YL HYDROPEROXIDE; 3,3 DIMETHYL 2,4 DIPHENYLBUTAN 2 YL HYDROPEROXIDE; 3,6 DIMETHYL 2 PHENYL 5 HEPTEN 2 YL HYDROPEROXIDE; 4 (2 METHYL 2 PROPENYLOXY) 2 METHYLBUTAN 2 YL HYDROPEROXIDE; 5 METHYL 2 PHENYL 5 HEXEN 2 YL HYDROPEROXIDE; 6 METHYL 2 PHENYL 5 HEPTEN 2 YL HYDROPEROXIDE; ACETOPHENONE; ALKADIENE; ALKENE; CARBON; COPPER COMPLEX; DIOXANE; HYDROPEROXIDE DERIVATIVE; PEROXIDE; PEROXY RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; DIMERIZATION; DRUG STRUCTURE; PEROXIDATION; REACTION ANALYSIS; SYNTHESIS;

ALKADIENES; ANTIMALARIALS; ARTEMISININS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PEROXIDES; SESQUITERPENES;

EID: 11844275287     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048359j     Document Type: Article

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39. Regioselectivity should be controlled by stability of the intermediate carbon-centered radical. Thus, the triethylsilyldioxy group tends to be introduced into the more substituted carbon of the C=C double bond.
40. (a) Gridnev, A. A.; Ittel, S. D.; Fryd, M.; Wayland, B. B. Organometallics 1996, 15, 222.
41. (b) Ohgo, Y.; Takeuchi, S. J. Chem. Soc., Chem. Commun. 1985, 21.
42. (c) Schrauzer, G. N. Angew. Chem., Int. Ed. Engl. 1976, 15, 417.
43. 1H NMR spectrum that deuterium atom transfer to the alkene 1 produced exclusively the triethylsilyl peroxide 2-d. Therefore, the lower deuterium incorporation into 4-d is attributed to the acid-promoted H-D exchange in desilylation step of 2-d.
44. Alkene peroxidation procedure requires an induction period, the length of which depends slightly on the structure of alkene. Therefore, comparisons of the alkene conversions as determined from separate reactions are not meaningful.
45. Regioselectivities observed for Co(II)-phorphyrin complex-catalyzed peroxidation of dienes can be interpreted by this notion: Sugamoto, K.; Matsushita, Y.; Matsui, T. J. Chem. Soc., Perkin Trans. 1 1998, 3989.
46. 18 were estimated to be 0 and 27°, respectively.
47. (a) Hariharan, P. C.; Pople, J. A. Theo. Chim. Acta. 1973, 28, 213.
48. (b) Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724.
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50. 20 cis-alkenes are more reactive than trans-alkenes. Moreover, substitution with a tert-butyl group decreases the reactivity of trans-alkene more markedly than the cis-alkene. More remarkable steric effects can be seen in a series of styrene derivatives.
51. Katsuki, T. Synlett 2003, 281.
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53. Several HCo(III) complexes are known to be acidic: (a) Nishinaga, A.; Yamada, T.; Fujisawa, H.; Ishizaki, K.; Ihara, H.; Matuura, T. J. Mol. Catal. 1988, 48, 249. (b) Chao, T.-H.; Espenson, J. H. J. Am. Chem. Soc. 1978, 100, 129. See also ref 12c.
54. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley-Interscience: 1994.
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63. 7j
64. 7j
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67. 32
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