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Volumn 34, Issue 8, 1993, Pages 1283-1286

Cyclizations wherein an epoxide acts as the source of initiation and termination steps. Evidence for an early transition state in biomimetic epoxide cyclizations

(3) Taylor, Stephen K a May, Scott A a Hopkins, Jeffrey A a

a HOPE COLLEGE (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; CYCLIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0027402761 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)91775-1 Document Type: Article

Times cited : (10)

References (18)

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5
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- BIOSYNTHETIC, BIOMIMETIC AND RELATED EPOXIDE CYCLIZATIONS. A REVIEW
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- Taylor¹

6
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- J.D. Morrison, Academic Press, New York, Chapter 5
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7
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10
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- and Correction
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- Taylor¹ Bischoff² Blankespoor³ Deck⁴ Harvey⁵ Johnson⁶ Marolweski⁷ Mork⁸ Motry⁹ Van¹⁰

11
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12
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- Certain aspects of the mechanism have been written as concerted for conciseness. However, the arrows do not necessarily indicate concerted processes.

13
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- 4.

14
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- The Cyclization of Epoxyolefins: The Reaction of Geraniolene Monoepoxide with Boron Fluoride Etherate
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- Goldsmith¹

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16
- 84918729778
- Products 4 and 5 account for 81% of the volatile product distribution of equation 2. Products analogous to those represented by 8 (see below) in equation 3 account for another 9% as shown by GCMS and an NMR of the mixture of isomers. We were unable to separate these isomers, but they would be expected to accompany 5 based on the precendent reaction in equation 3. There may also be a small amount of product where the double bond has rearranged to the tertiary position.

17
- 84918755108
- The yields of these products were undoubtedly higher, but these are the yields of pure, isolated compounds. Impure chromatograph fractions containing these comounds were not counted in the yields.

18
- 84918737022
- 5 For example, the Wittig reagent used in the synthesis of 3 was prepared from the phosphonium salt of 1-bromo-3-phenylbenzene and it was combined with 4-methyl-4-pentenal. The resulting aryldiene was epoxidized, yielding two isomeric epoxides in a ratio of approximately 1:1. These isomers were separated by HPLC. Specific Wittig and epoxidation procedures are given in the aforementioned article.

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