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

Tetrahedron letters

New diene formation by ene-type chlorination and palladium catalyzed dehydrochlorination: Synthesis of citral from diprenyl ether

S Suzuki, Y Fujita, T Nishida

Index: Suzuki, Shigeaki; Fujita, Yoshiji; Nishida, Takashi Tetrahedron Letters, 1983 , vol. 24, # 51 p. 5737 - 5740

Full Text: HTML

Citation Number: 11

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Synthesis of citral from diprenyl ether is achieved by new diene forming reaction which consists of ene-type chlorination and palladium catalyzed dehydrochlorination. ... : NMR (CDCl 3 , HMS) δ 1.65 (s, 3H); 1.74 (s, 3H); 1.81 (s, 3H); 3.62 (d, J = 6.9 Hz, 2H); 4.00 (d, J = 7.5 Hz, ...

3-chloro-2-methyl-4-(3-methylbut-2-enoxy)but-1-ene Structure

3-chloro-2-meth...

~%

3,3-dimethyl-2-prop-1-en-2-ylpent-4-enal Structure

3,3-dimethyl-2-...

3-methyl-1-(3-methylbuta-1,3-dienoxy)but-2-ene Structure

3-methyl-1-(3-m...

Citral Structure

3-chloro-2-methyl-4-(3-methylbut-2-enoxy)but-1-ene Structure

3-chloro-2-meth...

~66%

Citral Structure

(E)-4-(but-2-en-1-yloxy)-3-chloro-2-methylbut-1-ene Structure

(E)-4-(but-2-en...

~32%

3-methyl-2-propan-2-ylidenepent-4-enal Structure

3-methyl-2-prop...

(E)-1-(but-2-en-1-yloxy)-3-methylbut-2-ene Structure

(E)-1-(but-2-en...

~%

3-methyl-2-propan-2-ylidenepent-4-enal Structure

3-methyl-2-prop...

3-methyl-1-(2-methylprop-2-enoxy)but-2-ene Structure

3-methyl-1-(2-m...

~%

4-methyl-2-propan-2-ylidenepent-4-enal Structure

4-methyl-2-prop...

3-chloro-2-methyl-4-(2-methylprop-2-enoxy)but-1-ene Structure

3-chloro-2-meth...

~38%

4-methyl-2-propan-2-ylidenepent-4-enal Structure

4-methyl-2-prop...

3-chloro-2-methyl-4-(2-methylbut-3-en-2-yloxy)but-1-ene Structure

3-chloro-2-meth...

~44%

2-isopropylidene-5-methyl-hex-4-enal Structure

2-isopropyliden...

2,2-dimethyl-3-methylidene-4-prop-1-en-2-yloxolane Structure

2,2-dimethyl-3-...

3-methyl-3-[(3-methyl-2-butenyl)oxy]but-1-ene Structure

3-methyl-3-[(3-...

~%

2,2-dimethyl-3-methylidene-4-prop-1-en-2-yloxolane Structure

2,2-dimethyl-3-...

4-but-3-en-2-yloxy-3-chloro-2-methylbut-1-ene Structure

4-but-3-en-2-yl...

~26%

(E)-2-(propan-2-ylidene)hex-4-enal Structure

(E)-2-(propan-2...

2-methyl-3-methylidene-4-prop-1-en-2-yloxolane Structure

2-methyl-3-meth...

1-but-3-en-2-yloxy-3-methylbut-2-ene Structure

1-but-3-en-2-yl...

~%

2-methyl-3-methylidene-4-prop-1-en-2-yloxolane Structure

2-methyl-3-meth...

3-chloro-2-methyl-4-prop-2-enoxybut-1-ene Structure

3-chloro-2-meth...

~17%

2-propan-2-ylidenepent-4-enal Structure

2-propan-2-ylid...

3-methylidene-4-prop-1-en-2-yloxolane Structure

3-methylidene-4...

3-methyl-1-prop-2-enoxybut-2-ene Structure

3-methyl-1-prop...

~%

2-propan-2-ylidenepent-4-enal Structure

2-propan-2-ylid...

3-methyl-3-[(3-methyl-2-butenyl)oxy]but-1-ene Structure

3-methyl-3-[(3-...

~71%

3-chloro-2-methyl-4-(2-methylbut-3-en-2-yloxy)but-1-ene Structure

3-chloro-2-meth...

3-chloro-2-methyl-4-prop-2-enoxybut-1-ene Structure

3-chloro-2-meth...

~19%

2-propan-2-ylidenepent-4-enal Structure

2-propan-2-ylid...

3-methylidene-4-prop-1-en-2-yloxolane Structure

3-methylidene-4...

3-methyl-1-prop-2-enoxybut-2-ene Structure

3-methyl-1-prop...

~%

3-methylidene-4-prop-1-en-2-yloxolane Structure

3-methylidene-4...

3-chloro-2-methyl-4-(3-methylbut-2-enoxy)but-1-ene Structure

3-chloro-2-meth...

~%

3,3-dimethyl-2-prop-1-en-2-ylpent-4-enal Structure

3,3-dimethyl-2-...

3-methyl-1-(3-methylbuta-1,3-dienoxy)but-2-ene Structure

3-methyl-1-(3-m...

Citral Structure

1-but-3-en-2-yloxy-3-methylbut-2-ene Structure

1-but-3-en-2-yl...

~74%

4-but-3-en-2-yloxy-3-chloro-2-methylbut-1-ene Structure

4-but-3-en-2-yl...

3-methyl-1-prop-2-enoxybut-2-ene Structure

3-methyl-1-prop...

~74%

3-chloro-2-methyl-4-prop-2-enoxybut-1-ene Structure

3-chloro-2-meth...