Enediyne-and Tributyltin Hydride-Mediated Aryl Radical Additions onto Various Radical Acceptors

…, D Klingberg, S Meyenburg, BL Stallman

Index: Grissom, Janet Wisniewski; Klingberg, Detlef; Meyenburg, Sabine; Stallman, Brenda L. Journal of Organic Chemistry, 1994 , vol. 59, # 25 p. 7876 - 7888

Full Text: HTML

Citation Number: 48

Abstract

Tandem enediyne-radical cyclizations were carried out on substrates that contain nitrile and ketone radical acceptors. The products of these cyclizations and the previously reported tandem enediyneradical cyclizations containing aldehyde and oxime ether radical acceptors were compared with tributyltin hydride-mediated aryl radical addition reactions with 1- bromonaphthalene derivatives containing aldehyde, oxime ether, nitrile, and ketone ...

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1-Bromo-2-naphthalenebutanal Structure

159305-83-6

1-Bromo-2-napht...

~49%

4(1H)-Phenanthrenone,2,3-dihydro- Structure

778-48-3

4(1H)-Phenanthr...

1,2,3,4-tetrahydrophenanthren-4-ol Structure

56179-82-9

1,2,3,4-tetrahy...

4-naphthalen-2-ylbutanal Structure

100885-87-8

4-naphthalen-2-...

1-<WBR>Bromo-<WBR>2-<WBR>(bromomethyl)<WBR>naphthalene Structure

37763-43-2

1-<WBR>Bromo-<W...

~%

4-naphthalen-2-ylbutanal Structure

100885-87-8

4-naphthalen-2-...

1-Bromo-2-methylnaphthalene Structure

2586-62-1

1-Bromo-2-methy...

~%

4-naphthalen-2-ylbutanal Structure

100885-87-8

4-naphthalen-2-...

1-bromo-2-but-3-enylnaphthalene Structure

109433-16-1

1-bromo-2-but-3...

~%

4-naphthalen-2-ylbutanal Structure

100885-87-8

4-naphthalen-2-...

1-Bromo-2-naphthalenebutanol Structure

1026185-94-3

1-Bromo-2-napht...

~%

4-naphthalen-2-ylbutanal Structure

100885-87-8

4-naphthalen-2-...

1-<WBR>Bromo-<WBR>2-<WBR>(bromomethyl)<WBR>naphthalene Structure

37763-43-2

1-<WBR>Bromo-<W...

~%

3-naphthalen-2-ylpropanal Structure

136415-67-3

3-naphthalen-2-...

1-Bromo-2-methylnaphthalene Structure

2586-62-1

1-Bromo-2-methy...

~%

3-naphthalen-2-ylpropanal Structure

136415-67-3

3-naphthalen-2-...

1-bromo-2-but-3-enylnaphthalene Structure

109433-16-1

1-bromo-2-but-3...

~%

3-naphthalen-2-ylpropanal Structure

136415-67-3

3-naphthalen-2-...

1-Bromo-2-methylnaphthalene Structure

2586-62-1

1-Bromo-2-methy...

~%

(1-bromonaphthalen-2-yl)methanol Structure

76635-70-6

(1-bromonaphtha...

6-(2-Ethynylphenyl)-5-hexyn-2-one Structure

159306-06-6

6-(2-Ethynylphe...

~79%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

159305-89-2

N/A

~52%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

diiodobenzene Structure

615-42-9

diiodobenzene

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

1-<WBR>Bromo-<WBR>2-<WBR>(bromomethyl)<WBR>naphthalene Structure

37763-43-2

1-<WBR>Bromo-<W...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

1-Bromo-2-methylnaphthalene Structure

2586-62-1

1-Bromo-2-methy...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

1-BROMO-2-NAPHTHALDEHYDE Structure

3378-82-3

1-BROMO-2-NAPHT...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

(1-bromonaphthalen-2-yl)methanol Structure

76635-70-6

(1-bromonaphtha...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

150723-26-5

N/A

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

159305-88-1

N/A

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

150723-27-6

N/A

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

5-(2-((trimethylsilyl)ethynyl)phenyl)-4-pentynal Structure

150723-28-7

5-(2-((trimethy...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

159306-05-5

N/A

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

6-(2-((Trimethylsilyl)ethynyl)phenyl)-5-hexyn-2-ol Structure

159306-03-3

6-(2-((Trimethy...

~%

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

1-<WBR>Bromo-<WBR>2-<WBR>(bromomethyl)<WBR>naphthalene Structure

37763-43-2

1-<WBR>Bromo-<W...

allyl bromide Structure

106-95-6

allyl bromide

~%

1-bromo-2-but-3-enylnaphthalene Structure

109433-16-1

1-bromo-2-but-3...

6-(2-Ethynylphenyl)-5-hexyn-2-one Structure

159306-06-6

6-(2-Ethynylphe...

~5%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

N/A Structure

159305-89-2

N/A

~40%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

2-Butanone,4-(2-naphthalenyl)- Structure

68427-26-9

2-Butanone,4-(2...

diiodobenzene Structure

615-42-9

diiodobenzene

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

1-<WBR>Bromo-<WBR>2-<WBR>(bromomethyl)<WBR>naphthalene Structure

37763-43-2

1-<WBR>Bromo-<W...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

1-Bromo-2-methylnaphthalene Structure

2586-62-1

1-Bromo-2-methy...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

1-BROMO-2-NAPHTHALDEHYDE Structure

3378-82-3

1-BROMO-2-NAPHT...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

(1-bromonaphthalen-2-yl)methanol Structure

76635-70-6

(1-bromonaphtha...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

N/A Structure

150723-26-5

N/A

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

N/A Structure

159305-88-1

N/A

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

N/A Structure

150723-27-6

N/A

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

5-(2-((trimethylsilyl)ethynyl)phenyl)-4-pentynal Structure

150723-28-7

5-(2-((trimethy...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

N/A Structure

159306-05-5

N/A

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...

6-(2-((Trimethylsilyl)ethynyl)phenyl)-5-hexyn-2-ol Structure

159306-03-3

6-(2-((Trimethy...

~%

2,3-DIHYDRO-1H-BENZ[E]INDEN-1-ONE Structure

6342-87-6

2,3-DIHYDRO-1H-...


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