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Literature DB >> 20161263

An exceptionally simple and efficient synthesis of 6-methyl-6-vinylfulvene, and its oxidative transformations.

Abstract

A new efficient synthesis of 6-methyl-6-vinylfulvene was developed, starting from the 6-(2-hydroxyethyl)-6-methylfulvene. With larger quantities of the title compound in hand, its photooxygenation with singlet oxygen was studied. Cyclization of the cyclopropanone intermediate to both vinyl moieties in the unsaturated system was observed, whereas the saturated endoperoxide gave mostly the cyclopentenone derivative. m-CPBA attacks exclusively the endocyclic double bonds and gives the 3-cyclopentenones via the unstable epoxides.

Entities: Chemical Disease Gene

Year: 2009 PMID： 20161263 PMCID： PMC2700951 DOI： 10.1016/j.tetlet.2009.02.221

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

2 in total

1. Prostanoid endoperoxide model compounds: 2, 3-dioxabicyclo[2.2.1]heptane via selective diimide reduction.

Authors: W Adam; H J Eggelte
Journal: J Org Chem Date: 1977-11-25 Impact factor: 4.354

2. Synthesis of thermal reactivity of some 2,3-dioxabicyclo[2.2.1]heptane models of prostaglandin endoperoxides.

Authors: D J Coughlin; R G Salomon
Journal: J Am Chem Soc Date: 1977-01-19 Impact factor: 15.419

2 in total

9 in total

1. Pyrrolidine catalyzed reactions of cyclopentadiene with α,β-unsaturated carbonyl compounds: 1,2- versus 1,4-additions.

Authors: Necdet Coskun; Meliha Çetin; Scott Gronert; Jingxiang Ma; Ihsan Erden
Journal: Tetrahedron Date: 2015-05-06 Impact factor: 2.457

An exceptionally simple and efficient synthesis of 6-methyl-6-vinylfulvene, and its oxidative transformations.

1. Prostanoid endoperoxide model compounds: 2, 3-dioxabicyclo[2.2.1]heptane via selective diimide reduction.

2. Synthesis of thermal reactivity of some 2,3-dioxabicyclo[2.2.1]heptane models of prostaglandin endoperoxides.

1. Pyrrolidine catalyzed reactions of cyclopentadiene with α,β-unsaturated carbonyl compounds: 1,2- versus 1,4-additions.

2. Diverse modes of reactivity of 6-(chloromethyl)-6-methylfulvene.

3. Imidazolidin-4-ones via (3+2) cycloadditions of aza-oxyallyl cations onto (E)-Narylideneanilines.

4. Temperature-dependent, competitive 1,3-acyl shift versus decarbonylation of a cyclopropanone intermediate.

5. Unusual hydroxyl effect on fulvene endoperoxide decompositions.

6. An efficient catalytic method for fulvene synthesis.

7. 1,2-Dihydropentalenes from fulvenes by [6 + 2] cycloadditions with 1-isopropenylpyrrolidine.

8. An expedient synthesis of 6-vinylfulvene.

9. Effect of allylic groups on S(N)2 reactivity.