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Tetrahedron Letters

Volumn 24, Issue 19, 1983, Pages 2005-2008

A general synthetic method for 2,6-cyclodecadienone system by intramolecular alkylation of protected cyanohydrins

(3) Takahashi, Takashi a Nemoto, Hisao a Tsuji, Jiro a

a TOKYO INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001545525 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)81828-6 Document Type: Article

Times cited : (39)

References (23)

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3
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- Cope rearrangement of 1,2-divinylcyclohexane to 1,5-cyclodecadiene is reversible. Oxy-Cope rearrangement of 1,2-divinylcyclohexenol usually gives (Z,E)-cyclodecadienone. In contrast, Cope-Claisen rearrangement leads to 1,6-cyclodecadiene.

4
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5
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8
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- Grieco¹ Nishizawa²

9
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- (1977) J. Am. Chem. Soc. , vol.99 , pp. 4186
- Still¹

10
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- Still¹

11
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12
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13
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14
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15
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19
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- Evans¹ Hoffman² Truesdale³

20
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- 14, Another reason is that placing an E double bond in eight membered ring (γ attack product) is highly improbable. Moreover the cyclization product C has no acidic proton, hence the isomerization of the unsaturated cyanohydrin ether does not occur.

21
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22
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- 4) δ 5.93 [[Truncated]]

23
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- The isomerization of the less stable (E)-enone 15 to the more stable (Z)-enone 18 with base treatment is known
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- Still¹

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