Cyclopropanones. Formation of vinylcyclopropanols and their rearrangement to cyclobutanones

HH Wasserman, MJ Hearn…

Index: Wasserman, Harry H.; Hearn, Michael J.; Cochoy, Robert E. Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2874 - 2880

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Citation Number: 39

Abstract

Vinylcyclopropanols, formed by the addition of vinylmagnesium bromide to the ethyl hemiketal of cyclopropanone, may be converted to cyclobutanone derivatives on reaction with various electrophiles. The ring enlargement of 1-vinyl-2-methylcyclopropanol takes place by preferential migration of the more highly substituted carbon atom.

 Related Synthetic Route
1-isobutenylcyclopropanol Structure

73680-09-8

1-isobutenylcyc...

~0%

Mesityl oxide Structure

141-79-7

Mesityl oxide

5-methylhex-4-en-3-one Structure

13905-10-7

5-methylhex-4-e...

5-hydroxy-5-methylhexan-3-one Structure

59356-91-1

5-hydroxy-5-met...

N/A Structure

22935-31-5

N/A

~82%

2-methylcyclobutan-1-one Structure

1517-15-3

2-methylcyclobu...

N/A Structure

22935-31-5

N/A

~63%

1-Penten-3-one Structure

1629-58-9

1-Penten-3-one

2-methylcyclobutan-1-one Structure

1517-15-3

2-methylcyclobu...

1-isobutenylcyclopropanol Structure

73680-09-8

1-isobutenylcyc...

~0%

Mesityl oxide Structure

141-79-7

Mesityl oxide

5-methylhex-4-en-3-one Structure

13905-10-7

5-methylhex-4-e...

5-hydroxy-5-methylhexan-3-one Structure

59356-91-1

5-hydroxy-5-met...

1-vinyl-2-methylcyclopropanol Structure

73680-11-2

1-vinyl-2-methy...

~%

(2R,4S)-2,4-dimethylcyclobutan-1-one Structure

1605-00-1

(2R,4S)-2,4-dim...

(2S,4S)-2,4-dimethylcyclobutan-1-one Structure

1604-99-5

(2S,4S)-2,4-dim...

cis,trans-2.3-Dimethylcyclobutanon Structure

28113-36-2

cis,trans-2.3-D...

Detail

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