1,4-dioxene in organic synthesis: Substitution reactions of 2-(1,4- dioxenyl)-alkanol. Unusual formation of spirocyclopropane derivatives

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 863-866

  Hanna, Issam ^a   Ricard, Louis ^b  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b ECOLE POLYTECHNIQUE   (France)

Author keywords

2,3 dihydro 1,4 dioxin; Allylic alcohols; Lithium perchlorate; Nucleophilic substitution; Spirocyclopropane

Indexed keywords

ALKANOL; CYCLOPROPANE DERIVATIVE; DIOXIN; LITHIUM DERIVATIVE; ORGANIC COMPOUND; REAGENT; SPIROCYCLOPROPANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

OXY;

EID: 0033613805     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02541-6     Document Type: Article

References (14)

1. For recent studies on the use of dioxene in synthesis, see : (a) Hanna, I.; Prangé, T.; Zeghdoudi, R. Tetrahedron Lett. 1996, 37, 7013-7016.
2. (b) Baylon, C.; Hanna, I. Tetrahedron Lett. 1995, 36, 6475-6478.
3. (c) Hanna, I. Tetrahedron Lett. 1995, 36, 889-892
4. a) D. Boger, Y. Zhu, J. Org. Chem. 1994, 59, 3453-3458;
5. b) S. Horito, M. Amano and H. Hoshimoto, J. Carbohydr Chem. 1989, 8, 681-684.
6. Fétizon, M.; Goulaouic, P.; Hanna, L; Prangé, T. J. Org. Chem. 1988, 53, 5673-5679.
7. For a review see: Fétizon, M.; Goulaouic, P.; Hanna, I. Heterocycles, 1988, 28, 521-527.
8. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 2986-2987 and references cited therein.
9. Grieco, P. A.; Collins, J. L.; Henry, K. J. Tetrahedron Lett. 1992, 33, 4735-4738.
10. For the use of these conditions for addition of C-nucleophiles to acetals see: Fujioka, H.; Kitagawa, H.; Nagatomi, Y.; Kita, Y. Tetrahedron: Asymmetry 1995, 6, 2113-2116.
11. 2) ppm.
12. ω=0.061, G.O.F.=1.28.
13. Under these conditions, cyclobutanone derivatives prepared by the reaction of ketones and their acetals with 1,2-bis(trimethylsilyloxy)cyclobut-1-ene undergo acid-mediated rearrangement to 1,3-cyclopentanediones: Shimada, J.; Hashimoto, K.; Kim, B. H.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1759-1773. Wu, Y.-J;; Burnel, D. J. Tetrahedron Lett. 1988, 29, 369-4372.
14. Under these conditions, cyclobutanone derivatives prepared by the reaction of ketones and their acetals with 1,2-bis(trimethylsilyloxy)cyclobut-1-ene undergo acid-mediated rearrangement to 1,3-cyclopentanediones: Shimada, J.; Hashimoto, K.; Kim, B. H.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1759-1773. Wu, Y.-J;; Burnel, D. J. Tetrahedron Lett. 1988, 29, 369-4372.