Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agents

P Girard, JL Namy, HB Kagan

Index: Girard, P.; Namy, J. L.; Kagan, H. B. Journal of the American Chemical Society, 1980 , vol. 102, # 8 p. 2693 - 2698

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Citation Number: 1086

Abstract

Abstract: The facile synthesis of Smlz and Yblz from corresponding metals in THF is described. The reactivity of these potentially powerful reducing agents toward a variety of functional groups is tested. Epoxides and sulfoxides are deoxygenated. Aldehydes are selectively reduced in presence of a ketone. Alkyl halides or tosylates are converted into alkanes. Only coupling products are obtained from benzylic or allylic halides. In the ...

 Related Synthetic Route
2-Bromo-2-methylpropane Structure

507-19-7

2-Bromo-2-methy...

2-Octanone Structure

111-13-7

2-Octanone

~20%

2-Octanol Structure

4128-31-8

2-Octanol

5-methyl-5-undecanol Structure

21078-80-8

5-methyl-5-undecanol

Detail
2-Bromobutane Structure

78-76-2

2-Bromobutane

2-Octanone Structure

111-13-7

2-Octanone

~5%

2-Octanol Structure

4128-31-8

2-Octanol

5-methyl-5-undecanol Structure

21078-80-8

5-methyl-5-undecanol

Detail
1-Bromo-2-methylpropane Structure

78-77-3

1-Bromo-2-methy...

2-Octanone Structure

111-13-7

2-Octanone

~5%

2-Octanol Structure

4128-31-8

2-Octanol

5-methyl-5-undecanol Structure

21078-80-8

5-methyl-5-undecanol

Detail
Butyl iodide Structure

542-69-8

Butyl iodide

2-Octanone Structure

111-13-7

2-Octanone

~3%

2-Octanol Structure

4128-31-8

2-Octanol

5-methyl-5-undecanol Structure

21078-80-8

5-methyl-5-undecanol

Detail
Methyl octylate Structure

111-11-5

Methyl octylate

methyl iodide Structure

74-88-4

methyl iodide

~10%

2-Nonanol, 2-methyl- Structure

10297-57-1

2-Nonanol, 2-methyl-

Oxirane,2-(phenylmethyl)- Structure

4436-24-2

Oxirane,2-(phen...

~0%

Allylbenzene Structure

300-57-2

Allylbenzene

1-Phenyl-2-propanol Structure

698-87-3

1-Phenyl-2-propanol

Phenylacetone Structure

103-79-7

Phenylacetone

cis-9-oxabicyclo[6.1.0]nonane Structure

4925-71-7

cis-9-oxabicycl...

~95%

Cyclooctene Structure

931-88-4

Cyclooctene

Oxirane, 2-octyl- Structure

2404-44-6

Oxirane, 2-octyl-

~92%

2-decanol Structure

1120-06-5

2-decanol

1-decene Structure

872-05-9

1-decene

2-Decanone Structure

693-54-9

2-Decanone

(+/-)-trans-5,6-epoxydecane Structure

2165-61-9

(+/-)-trans-5,6...

~17%

5-Decene, (5E)- Structure

7433-56-9

5-Decene, (5E)-

5-Decanol Structure

5205-34-5

5-Decanol

methyl 10-(tosyloxy)decanoate Structure

74120-71-1

methyl 10-(tosy...

2-Octanone Structure

111-13-7

2-Octanone

~15%

Methyl Caprate Structure

110-42-9

Methyl Caprate

methyl 10-iododecanoate Structure

53602-13-4

methyl 10-iodod...

Detail
Oxirane, 2-octyl- Structure

2404-44-6

Oxirane, 2-octyl-

~0%

2-decanol Structure

1120-06-5

2-decanol

1-decene Structure

872-05-9

1-decene

2-Decanone Structure

693-54-9

2-Decanone

p-Tolyl ethyl sulfoxide Structure

6378-07-0

p-Tolyl ethyl s...

~77%

Benzene, 1-(ethylthio)-4-methyl- Structure

622-63-9

Benzene, 1-(eth...

Oxirane,2-(phenylmethyl)- Structure

4436-24-2

Oxirane,2-(phen...

~83%

Allylbenzene Structure

300-57-2

Allylbenzene

1-Phenyl-2-propanol Structure

698-87-3

1-Phenyl-2-propanol

Phenylacetone Structure

103-79-7

Phenylacetone

ALLYL CHLORIDE Structure

107-05-1

ALLYL CHLORIDE

2-Octanone Structure

111-13-7

2-Octanone

~60%

4-methyldec-1-en-4-ol Structure

38564-33-9

4-methyldec-1-e...

1-methylsulfinylnaphthalene Structure

29959-93-1

1-methylsulfiny...

~92%

1-methylsulfanylnaphthalene Structure

10075-72-6

1-methylsulfany...


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