e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

On the regioselectivity of elimination reactions in terpene derivatives

B Badet, M Julia, JM Mallet, C Schmitz

Index: Badet,B.; Julia,M.; Mallet,J.M. Tetrahedron, 1988 , vol. 44, p. 2913

Full Text: HTML

Citation Number: 8

Abstract

Tertiary alcohols with prenyl or geranyl moities, bearing a second oxygen. function in the 3, 4 or 5 position were dehydrated under various conditions: the composition of the olefinic mixture obtained was accounted for, by an intramolecular base relay effect. Basic elimination of analogous dimethylsutfonium salts gave results that could be related to the inductive effect: a correlation between regioselectivity and the Taft constantσI of the ...

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

Learn More

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

Learn More

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

UNII:W5970P28N3 Structure

UNII:W5970P28N3

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

Learn More

2-Methyl-2,4-butanediol Structure

2-Methyl-2,4-bu...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

Learn More

O-Acetyl-2-methylpentane-2,5-diol Structure

O-Acetyl-2-meth...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

Learn More

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

Learn More

6-Methylhept-5-en-2-one Structure

6-Methylhept-5-...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

Learn More

4,8-dimethyl-7-nonene-1,4-diol Structure

4,8-dimethyl-7-...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

Learn More

1-acetoxy-4,8-dimethyl-7-nonen-4-ol Structure

1-acetoxy-4,8-d...

~%

acetic acid,4,8-dimethylnona-3,7-dien-1-ol Structure

acetic acid,4,8...

(E)-4,8-dimethylnona-4,7-dien-1-yl acetate Structure

(E)-4,8-dimethy...

(Z)-4,8-dimethylnona-3,7-dien-1-yl acetate Structure

(Z)-4,8-dimethy...

Detail Learn More

4-methylpentane-1,4-diol Structure

4-methylpentane...

~0%

2,2-dimethyltetrahydrofuran Structure

2,2-dimethyltet...

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

Learn More

2-Methyl-1-octene Structure

2-Methyl-1-octene

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

Learn More

2-Octanol, 2-methyl Structure

2-Octanol, 2-methyl

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

2-Methyl-1-octene Structure

2-Methyl-1-octene

Learn More

ISOPRENOL Structure

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(±)-3,7-dimethyloct-6-ene-1,3-diol Structure

(±)-3,7-dimethy...

7-Methyl-3-methylene-6-octen-1-ol Structure

7-Methyl-3-meth...

Detail Learn More

3-Buten-1-ol,3-methyl-, 1-(4-methylbenzenesulfonate) Structure

3-Buten-1-ol,3-...

~%

5-Methyl-5-hexenoic acid methyl ester Structure

5-Methyl-5-hexe...

Learn More

2-Octanol, 2-methyl Structure

2-Octanol, 2-methyl

~%

2-METHYL-2-OCTENE Structure

2-METHYL-2-OCTENE

2-Methyl-1-octene Structure

2-Methyl-1-octene

Learn More

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

tangerine acetate Structure

tangerine acetate

Detail Learn More

2-Methyl-2,4-butanediol Structure

2-Methyl-2,4-bu...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

2-acetoxy-6-methyl-6-heptene Structure

2-acetoxy-6-met...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

5-Chloro-2-pentanol Structure

5-Chloro-2-pentanol

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

6-Methylhept-5-en-2-one Structure

6-Methylhept-5-...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

dimethyl-5-hexen-1-yl acetate Structure

dimethyl-5-hexe...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

6,10-dimethyl-9-undecene-2,6-diol Structure

6,10-dimethyl-9...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

Learn More

1-acetoxy-6,10-dimethyl-9-undecen-6-ol Structure

1-acetoxy-6,10-...

~%

(Z)-tangerine acetate Structure

(Z)-tangerine a...

tangerine acetate Structure

tangerine acetate

(E)-6,10-dimethylundeca-6,9-dien-2-yl acetate Structure

(E)-6,10-dimeth...

Detail Learn More

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

~%

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

Learn More

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

Learn More

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

Learn More

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

tetrahydro-2,2,6-trimethyl-2H-pyran Structure

tetrahydro-2,2,...

sulcatol Structure

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

Learn More

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methyl-3-butanol Structure

1-(2-chloro-1,1...

~%

4-(2-chloro-1,1,2-trifluoroethoxy)-2-methylbut-1-ene Structure

4-(2-chloro-1,1...

1-(2-chloro-1,1,2-trifluoroethoxy)-3-methylbut-2-ene Structure

1-(2-chloro-1,1...

Learn More

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

Learn More

4-methylpentane-1,4-diol Structure

4-methylpentane...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

Learn More

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

Phenol Structure

~48%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

Learn More

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

~%

4-methylpent-3-enoxybenzene Structure

4-methylpent-3-...

Learn More

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

tetrahydro-2,2,6-trimethyl-2H-pyran Structure

tetrahydro-2,2,...

sulcatol Structure

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

Learn More

1-butoxy-3-methyl-3-butanol Structure

1-butoxy-3-meth...

~%

4-butoxy-2-methylbut-1-ene Structure

4-butoxy-2-meth...

2-Butene, 1-butoxy-3-methyl Structure

2-Butene, 1-but...

Learn More

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

Phenol Structure

~47%

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

Learn More

4-methylpentane-1,4-diol Structure

4-methylpentane...

~%

4-methylpent-4-enoxybenzene Structure

4-methylpent-4-...

Learn More

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

Learn More

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

Learn More

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

~%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

Learn More

sulcatol Structure

Phenol Structure

~53%

6-methylhept-5-en-2-yloxybenzene Structure

6-methylhept-5-...

Learn More

O-Acetyl-2-methylpentane-2,5-diol Structure

O-Acetyl-2-meth...

~%

acetic acid,4-methylpent-3-en-1-ol Structure

acetic acid,4-m...

Learn More

4-methylpentane-1,4-diol Structure

4-methylpentane...

~63%

2,2-dimethyltetrahydrofuran Structure

2,2-dimethyltet...

4-methyl-3-penten-1-ol Structure

4-methyl-3-pent...

4-Methyl-4-penten-1-ol Structure

4-Methyl-4-pent...

Learn More

1-Acetoxy-3-methyl-3-butanol Structure

1-Acetoxy-3-met...

~%

Prenyl acetate Structure

isoprenyl acetate Structure

isoprenyl acetate

Learn More

ISOPRENOL Structure

2-Methyl-3-buten-2-ol Structure

2-Methyl-3-bute...

~%

(±)-3,7-dimethyloct-6-ene-1,3-diol Structure

(±)-3,7-dimethy...

7-Methyl-3-methylene-6-octen-1-ol Structure

7-Methyl-3-meth...

Detail Learn More

6-methylhept-6-en-2-ol Structure

6-methylhept-6-...

Phenol Structure

~52%

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

Learn More

2-methylheptane-2,6-diol Structure

2-methylheptane...

~%

6-methylhept-6-en-2-yloxybenzene Structure

6-methylhept-6-...

Learn More

Prenylation of isopentenyl derivatives with 2-methyl-3-buten...

[Julia, M.; Schmitz, C. Bulletin de la Societe Chimique de France, 1986 , # 4 p. 630 - 636]