Novel nucleophilic substitution reaction by radical cation intermediates. Photosensitized transacetalization via SON1 mechanism

S Hashimoto, I Kurimoto, Y Fujii…

Index: Hashimoto, S.; Kurimoto, I.; Fujii, Y.; Noyori, R. Journal of the American Chemical Society, 1985 , vol. 107, # 5 p. 1427 - 1429

Full Text: HTML

Citation Number: 22

Abstract

DCNB: p-dicyanobenzene tertiary alcohol or weakly nucleophilic phenol was employed, 3, 4- dihydro-2H-pyran was formed as a major byprod~ ct.~ The stereochemistry of the transacetalization is to be noted. When irradiation of an equimolar mixture of cis-or trans-6- methyltetrahydropyran-2-yl ether 4 and an alcohol was conducted

 Related Synthetic Route
2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

Phenol Structure

108-95-2

Phenol

~16%

3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

2-Phenoxytetrahydropyran Structure

4203-50-3

2-Phenoxytetrah...

Detail
1-Octanol Structure

111-87-5

1-Octanol

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~88%

2-OCTYLOXYTETRAHYDRO-2H-PYRAN Structure

70690-19-6

2-OCTYLOXYTETRA...

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

(Trimethylsilyl)octyl ether Structure

14246-16-3

(Trimethylsilyl...

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~53%

2-OCTYLOXYTETRAHYDRO-2H-PYRAN Structure

70690-19-6

2-OCTYLOXYTETRA...

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

1-Octanol Structure

111-87-5

1-Octanol

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~80%

2-OCTYLOXYTETRAHYDRO-2H-PYRAN Structure

70690-19-6

2-OCTYLOXYTETRA...

1-Octanol Structure

111-87-5

1-Octanol

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~0%

2-OCTYLOXYTETRAHYDRO-2H-PYRAN Structure

70690-19-6

2-OCTYLOXYTETRA...

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

1-Octanol Structure

111-87-5

1-Octanol

N/A Structure

94800-77-8

N/A

~0%

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

N/A Structure

94800-80-3

N/A

1-Octanol Structure

111-87-5

1-Octanol

N/A Structure

94800-76-7

N/A

~0%

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

N/A Structure

94800-79-0

N/A

(Trimethylsilyl)octyl ether Structure

14246-16-3

(Trimethylsilyl...

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~0%

2-OCTYLOXYTETRAHYDRO-2H-PYRAN Structure

70690-19-6

2-OCTYLOXYTETRA...

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

Benzyl alcohol Structure

100-51-6

Benzyl alcohol

~0%

2-BENZYLOXYTETRAHYDROPYRAN Structure

1927-62-4

2-BENZYLOXYTETR...

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

Cyclohexanol Structure

108-93-0

Cyclohexanol

~0%

2-cyclohexyloxyoxane Structure

709-83-1

2-cyclohexyloxyoxane

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

2-Hexanol, 2-methyl- Structure

625-23-0

2-Hexanol, 2-methyl-

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~0%

3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

Detail
2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

Phenol Structure

108-95-2

Phenol

~0%

3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

2-Phenoxytetrahydropyran Structure

4203-50-3

2-Phenoxytetrah...

Detail
2-Hexanol, 2-methyl- Structure

625-23-0

2-Hexanol, 2-methyl-

2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

~0%

3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

2,4,6-Trimethylphenol Structure

527-60-6

2,4,6-Trimethyl...

Detail
2-(2,4,6-trimethylphenoxy)oxane Structure

94800-75-6

2-(2,4,6-trimet...

Phenol Structure

108-95-2

Phenol

~0%

3,4-Dihydro-2H-pyran Structure

110-87-2

3,4-Dihydro-2H-pyran

2-Phenoxytetrahydropyran Structure

4203-50-3

2-Phenoxytetrah...

Detail

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