Intramolecular radical cyclization of 2-haloethanal allyl acetal and allyl 2-halophenyl ether with a grignard reagent in the presence of iron(II) chloride

Tetrahedron Letters

Volumn 39, Issue 1-2, 1998, Pages 63-66

  Hayashi, Yasuhiro ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALLYL COMPOUND; BENZOFURAN DERIVATIVE; ETHER DERIVATIVE; FERROUS CHLORIDE; ORGANIC COMPOUND; RADICAL; REAGENT; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0031973382     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10489-0     Document Type: Article

References (18)

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9. The reaction of 1a with i-PrMgBr provided a mixture of 2a and 3a in almost the same ratio as that with n-BuMgBr.
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12. For a recent review on alkyl iron ate complex, see: Kauffmann, T. Angew. Chem. Int. Ed. Engl., 1996, 35, 386-403.
13. 3FeLi have been reported. Corey, E.J.; Posner, G.H. Tetrahedron Lett. 1970, 315-318.
14. 2O could not afford any deuterated product, either.
15. Recently, nickel or cobalt-catalyzed radical cyclization reaction has been reported. Vaupel, A.; Knochel, P. Tetrahedron Lett., 1994, 35, 8349-8352; Bamhaoud, T.; Prandi, J. J. Chem. Soc. Chem. Commun., 1996, 1229-1230.
16. Recently, nickel or cobalt-catalyzed radical cyclization reaction has been reported. Vaupel, A.; Knochel, P. Tetrahedron Lett., 1994, 35, 8349-8352; Bamhaoud, T.; Prandi, J. J. Chem. Soc. Chem. Commun., 1996, 1229-1230.
17. The ease of recombination providing 6 might be attributed to the stability of radical 5. A tertial radical derived from 1a could be stable enough to recombine with R[Fe] species. In contrast, a primary radical generated from 1b abstracts hydrogen more easily.
18. Cyclization of allyl 2-iodophenyl ether into a benzofuran derivative mediated by organozincate was also reported. Uchiyama, M.; Koike, M.; Kameda, M.; Kondo, Y.; Sakamoto, T. J. Am. Chem. Soc., 1996, 118, 8733-8734.