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Volumn 27, Issue 31, 1986, Pages 3565-3568

Lewis acid catalyzed rearrangements of structurally related α,β-unsaturated epoxy ketones and oximes. A complementary approach to the synthesis of isomeric 1,4-diketospiro[n,m] alkanes.

(3) Bach, Robert D a Tubergen, Mark W a Klix, Russell C a

a WAYNE STATE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001110848 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)84850-9 Document Type: Article

Times cited : (26)

References (13)

1
- 0012939455
- and references therein
- (1984) J. Org. Chem. , vol.49 , pp. 4181
- Bach¹ Domagala²

2
- 0000777075
- (1985) J. Org. Chem. , vol.50 , pp. 5438
- Bach¹ Klix²

3
- 13344296403
- (1985) Tetrahedron Lett. , pp. 985
- Bach¹ Klix²

4
- 37049091444
- Chem. Commun.
- (1984) J. Chem. Soc. , pp. 1472
- Bach¹ Domagala²

5
- 0003050412
- Corey has reported a novel α-alkylation of α,β-epoxy oximes by a base induced α-oxirane cleavage in tandem with a dimethyl cuprate addition to the vinyl nitroso intermediate.
- (1975) Tetrahedron Lett. , pp. 3117
- Corey¹ Melvin² Haslanger³

6
- 84918479281
- Denmark has reported that isophorone oxime under basic condition dimerizes.
- (1984) J. Org. Chem. , pp. 49
- Denmark¹ Dappen²

7
- 0000685449
- .alpha.-Chloro ketoximes as precursors of nitrosoalkenes: preparation, stereochemistry and conformation
- Denmark has reported that isophorone oxime under basic condition dimerizes.
- (1984) The Journal of Organic Chemistry , pp. 798
- Denmark¹ Dappen²

8
- 84985143848
- Synthetische Verwendung von Epoxynitronen. I.N-(2,3-Epoxypropyliden)-cyclohexylamin-oxid, ein neues Reagens zur Synthese von ?-Methyliden-?-lactonen aus Olefinen
- Opening of the epoxide has also been noted by Graf in reactions of α,β-epoxynitrones.
- (1979) Helvetica Chimica Acta , vol.62 , pp. 205
- Riediker¹ Graf²

9
- 0000664225
- (1971) Tetrahedron Lett. , pp. 195
- Timms¹ Wildsmith²

10
- 84918462814
- (1973) Can. J. Chem. , pp. 7173
- Lee-Ruff¹ Khanzanie²

11
- 25444509749
- Acid Catalyzed Rearrangements of Conjugated Cyclopropyl and Epoxy Ketones
- (1975) Canadian Journal of Chemistry , pp. 1708
- Lee-Ruff¹ Khanzanie²

12
- 84987339808
- Photochemische Reaktionen. 71. Mitteilung. Die Photoisomerisierung eines spirocyclischen ?, ?-Epoxyketons
- (1973) Helvetica Chimica Acta , vol.56 , pp. 239
- Wuthrich¹ Sienwinski² Schaffner³ Jeger⁴

13
- 84918462813
- Related examples that have been successful in this reaction include oximes of β-substituted cyclohexenone epoxides, substituted 1,2-epoxybicyclo[4.4.0]decanes and the oxime of compound 5. These rearrangements will be reported in detail elsewhere.

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