Tetrahedron letters

Preparation of 2-vinylcyclobutanones and their conversion to cyclopentenones

DA Jackson, M Rey, AS Dreiding

Index: Jackson, David A.; Rey, Max; Dreiding, Andre S. Tetrahedron Letters, 1983 , vol. 24, # 44 p. 4817 - 4820

Full Text: HTML

Citation Number: 22

Abstract

Abstract: Methyl-and ethyl-vinylketene 2 were added to several simple olefins 1 to afford alkylated 2-vinylcyclobutanones 4, which in turn rearranged to cyclopentenones 5 (via dienones g, l) or l (via 1, 2-acyl migration) under acid catalysis. Evidence is presented for a cyclopropyl-carbinyl intermediate 8.

 Related Synthetic Route
trans-2-Methyl-2-butenoyl chloride Structure

35660-94-7

trans-2-Methyl-...

METHYLENECYCLOPENTANE Structure

1528-30-9

METHYLENECYCLOP...

~79%

3-ethenyl-3-methylspiro[3.4]octan-2-one Structure

89237-37-6

3-ethenyl-3-met...

trans-2-Methyl-2-butenoyl chloride Structure

35660-94-7

trans-2-Methyl-...

Cyclohexane, methylene- Structure

1192-37-6

Cyclohexane, me...

~42%

3-ethenyl-3-methylspiro[3.5]nonan-2-one Structure

89237-38-7

3-ethenyl-3-met...

2-Butenoyl chloride, 2-ethyl-, (2E) Structure

89609-12-1

2-Butenoyl chlo...

METHYLENECYCLOPENTANE Structure

1528-30-9

METHYLENECYCLOP...

~67%

3-ethenyl-3-ethylspiro[3.4]octan-2-one Structure

89237-43-4

3-ethenyl-3-eth...

Cyclohexane, methylene- Structure

1192-37-6

Cyclohexane, me...

~%

3,4-dimethylspiro[4.5]dec-3-en-2-one Structure

89237-56-9

3,4-dimethylspi...

3-ethenyl-3-ethylspiro[3.4]octan-2-one Structure

89237-43-4

3-ethenyl-3-eth...

~49%

N/A Structure

97843-83-9

N/A

(3E)-1-(cyclopent-1-enyl)-3-ethyl-3-penten-2-one Structure

97843-82-8

(3E)-1-(cyclope...

3-ethyl-4-methylspiro[4.4]non-3-en-2-one Structure

89237-57-0

3-ethyl-4-methy...

2-methyl-3-pentyl-2-vinylcyclobutanone Structure

344408-07-7

2-methyl-3-pent...

~52%

2,3-dimethyl-5-pentylcyclopent-2-en-1-one Structure

89237-62-7

2,3-dimethyl-5-...

2,3-dimethyl-4-pentylcyclopent-2-en-1-one Structure

89237-58-1

2,3-dimethyl-4-...

Hept-1-ene Structure

592-76-7

Hept-1-ene

~%

2,3-dimethyl-4-pentylcyclopent-2-en-1-one Structure

89237-58-1

2,3-dimethyl-4-...

trans-2-Methyl-2-butenoyl chloride Structure

35660-94-7

trans-2-Methyl-...

~%

2,3-dimethyl-4-pentylcyclopent-2-en-1-one Structure

89237-58-1

2,3-dimethyl-4-...

2-methyl-3-pentyl-2-vinylcyclobutanone Structure

344408-07-7

2-methyl-3-pent...

~11%

2,3-dimethyl-5-pentylcyclopent-2-en-1-one Structure

89237-62-7

2,3-dimethyl-5-...

2,3-dimethyl-4-pentylcyclopent-2-en-1-one Structure

89237-58-1

2,3-dimethyl-4-...

Hept-1-ene Structure

592-76-7

Hept-1-ene

~%

2,3-dimethyl-5-pentylcyclopent-2-en-1-one Structure

89237-62-7

2,3-dimethyl-5-...

3-butyl-2,3-dimethyl-2-vinylcyclobutanone Structure

344408-83-9

3-butyl-2,3-dim...

~64%

N/A Structure

97843-75-9

N/A

N/A Structure

97843-73-7

N/A

4-butyl-2,3,4-trimethylcyclopent-2-en-1-one Structure

89237-54-7

4-butyl-2,3,4-t...

1-Hexene, 2-methyl- Structure

6094-02-6

1-Hexene, 2-methyl-

~%

4-butyl-2,3,4-trimethylcyclopent-2-en-1-one Structure

89237-54-7

4-butyl-2,3,4-t...

3-ethenyl-3-methylspiro[3.4]octan-2-one Structure

89237-37-6

3-ethenyl-3-met...

~71%

N/A Structure

97843-81-7

N/A

N/A Structure

97843-80-6

N/A

3,4-dimethylspiro[4.4]non-3-en-2-one Structure

89237-55-8

3,4-dimethylspi...

trans-2-Methyl-2-butenoyl chloride Structure

35660-94-7

trans-2-Methyl-...

~%

3,4-dimethylspiro[4.5]dec-3-en-2-one Structure

89237-56-9

3,4-dimethylspi...


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