Regioselective synthesis of cyclopentenones from 4-thianone

H Matsuyama, Y Miyazawa, Y Takei…

Index: Matsuyama, Haruo; Miyazawa, Yasuyuki; Takei, Yuji; Kobayashi, Michio Journal of Organic Chemistry, 1987 , vol. 52, # 9 p. 1703 - 1710

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Citation Number: 37

Abstract

&: ooc" a"(a) RX, K2C03, acetone reflux;(b) RX, Me2S0, 25" C;(c) LiC1, HMPA, 80" C, or NaCl, wet Me2S0, 150" C. active functional group for a ring transformation. However, organic syntheses using 4-thianone have been little studied and only a few examples ...

 Related Synthetic Route
2,3-dihydro-4H-thiopyran-4-one Structure

57242-69-0

2,3-dihydro-4H-...

~%

3-pentylcyclopent-2-en-1-one Structure

53253-07-9

3-pentylcyclope...

2-(p-tolylsulfonyl)-4-thianone Structure

104804-78-6

2-(p-tolylsulfo...

~%

3-pentylcyclopent-2-en-1-one Structure

53253-07-9

3-pentylcyclope...

7-(p-tolylsulfonyl)-1,4-dioxa-8-thiaspiro[4.5]decane 8,8-dioxide Structure

104804-79-7

7-(p-tolylsulfo...

~%

3-pentylcyclopent-2-en-1-one Structure

53253-07-9

3-pentylcyclope...

7-n-pentyl-7-(p-tolylsulfonyl)-1,4-dioxa-8-thiaspiro[4.5]-decane 8,8-dioxide Structure

104804-83-3

7-n-pentyl-7-(p...

~%

3-pentylcyclopent-2-en-1-one Structure

53253-07-9

3-pentylcyclope...

N/A Structure

107617-10-7

N/A

~%

3-pentylcyclopent-2-en-1-one Structure

53253-07-9

3-pentylcyclope...

N/A Structure

91791-17-2

N/A

~82%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

2-prop-2-enylcyclopent-3-en-1-one Structure

61020-31-3

2-prop-2-enylcy...

5-prop-2-enylcyclopent-2-en-1-one Structure

61020-32-4

5-prop-2-enylcy...

Methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate Structure

4160-61-6

Methyl 4-oxotet...

~%

2-prop-2-enylcyclopent-3-en-1-one Structure

61020-31-3

2-prop-2-enylcy...

Tetrahydrothiopyran-4-one Structure

1072-72-6

Tetrahydrothiop...

~%

2-prop-2-enylcyclopent-3-en-1-one Structure

61020-31-3

2-prop-2-enylcy...

N/A Structure

91791-17-2

N/A

~0%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

2-prop-2-enylcyclopent-3-en-1-one Structure

61020-31-3

2-prop-2-enylcy...

5-prop-2-enylcyclopent-2-en-1-one Structure

61020-32-4

5-prop-2-enylcy...

Methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate Structure

4160-61-6

Methyl 4-oxotet...

~%

5-prop-2-enylcyclopent-2-en-1-one Structure

61020-32-4

5-prop-2-enylcy...

Tetrahydrothiopyran-4-one Structure

1072-72-6

Tetrahydrothiop...

~%

5-prop-2-enylcyclopent-2-en-1-one Structure

61020-32-4

5-prop-2-enylcy...

Methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate Structure

4160-61-6

Methyl 4-oxotet...

~89%

Tetrahydrothiopyran-4-one Structure

1072-72-6

Tetrahydrothiop...

N/A Structure

91791-17-2

N/A

~0%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

2-prop-2-enylcyclopent-3-en-1-one Structure

61020-31-3

2-prop-2-enylcy...

5-prop-2-enylcyclopent-2-en-1-one Structure

61020-32-4

5-prop-2-enylcy...

Methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate Structure

4160-61-6

Methyl 4-oxotet...

~%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

Tetrahydrothiopyran-4-one Structure

1072-72-6

Tetrahydrothiop...

~%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

N/A Structure

97694-65-0

N/A

~%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

6-allyl-1,4-dioxa-8-thiaspiro[4.5]decane Structure

91791-07-0

6-allyl-1,4-dio...

~%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...

N/A Structure

91791-12-7

N/A

~%

2-prop-2-enylcyclopent-2-en-1-one Structure

51557-85-8

2-prop-2-enylcy...


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