Tetrahedron

Synthesis and photochromic properties of substituted 3H-naphtho [2, 1-b] pyrans

…, BM Heron, AC Instone, PN Horton, MB Hursthouse

Index: Gabbutt, Christopher D.; Heron, B. Mark; Instone, Alicia C.; Horton, Peter N.; Hursthouse, Michael B. Tetrahedron, 2005 , vol. 61, # 2 p. 463 - 471

Full Text: HTML

Citation Number: 38

Abstract

The synthesis and spectroscopic properties of novel 3H-naphtho [2, 1-b] pyrans are described. Subtle variation of the colour of the photo-generated merocyanine dyes derived from these naphthopyrans can be accomplished by controlling the steric interactions between a terminal pyrrolidine donor group and a proximal substituent.

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3-Amino-4-chlor...

~%

(3-bromo-4-chlorophenyl)-phenylmethanone Structure

782-03-6

(3-bromo-4-chlo...

3-Bromo-4-chlorobenzoic acid Structure

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3-Bromo-4-chlor...

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(3-bromo-4-chlorophenyl)-phenylmethanone Structure

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(3-bromo-4-chlo...

3-Bromo-4-chlorobenzoyl chloride Structure

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(3-bromo-4-chlorophenyl)-phenylmethanone Structure

782-03-6

(3-bromo-4-chlo...

N-Methoxy-N-methylbenzamide Structure

6919-61-5

N-Methoxy-N-met...

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(3-methoxy-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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5-Bromo-2-chloroanisole Structure

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5-Bromo-2-chlor...

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(3-methoxy-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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Pyrrolidine Structure

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(4-chloro-3-met...

~40%

(3-methoxy-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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(3-methoxy-4-py...

3-Bromo-4-chlorobenzoic acid Structure

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3-Bromo-4-chlor...

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3-Bromo-4-chlorobenzoyl chloride Structure

21900-34-5

3-Bromo-4-chlor...

3-Amino-4-chlorobenzoic acid Structure

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3-Amino-4-chlor...

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3-Bromo-4-chlorobenzoyl chloride Structure

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1-(3-iodo-4-pyrrolidinophenyl)-1-phenylprop-2-yn-1-ol Structure

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1-(3-iodo-4-pyr...

2-Naphthol Structure

135-19-3

2-Naphthol

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1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

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(4-chloro-3-iodophenyl)-phenylmethanone Structure

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1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

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(3-iodo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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~%

1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

834895-42-0

1-[2-iodo-4-(3-...

4-Chloro-3-iodobenzoic acid Structure

42860-04-8

4-Chloro-3-iodo...

~%

1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

834895-42-0

1-[2-iodo-4-(3-...

3-Amino-4-chlorobenzoic acid Structure

2840-28-0

3-Amino-4-chlor...

~%

1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

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1-[2-iodo-4-(3-...

4-chloro-3-iodobenzoyl chloride Structure

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4-chloro-3-iodo...

~%

1-[2-iodo-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

834895-42-0

1-[2-iodo-4-(3-...

1-(3-fluoro-4-pyrrolidinophenyl)-1-phenylprop-2-yn-1-ol Structure

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1-(3-fluoro-4-p...

2-Naphthol Structure

135-19-3

2-Naphthol

~70%

1-[2-fluoro-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

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1-[2-fluoro-4-(...

N/A Structure

314040-09-0

N/A

~%

1-[2-fluoro-4-(3-phenylbenzo[f]chromen-3-yl)phenyl]pyrrolidine Structure

834895-45-3

1-[2-fluoro-4-(...

3-Amino-4-chlorobenzoic acid Structure

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3-Amino-4-chlor...

~%

(4-chloro-3-iodophenyl)-phenylmethanone Structure

834895-49-7

(4-chloro-3-iod...

4-Chloro-3-iodobenzoic acid Structure

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4-Chloro-3-iodo...

~%

(4-chloro-3-iodophenyl)-phenylmethanone Structure

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(4-chloro-3-iod...

benzene Structure

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benzene

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(4-chloro-3-iodophenyl)-phenylmethanone Structure

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(4-chloro-3-iod...

N-Methoxy-N-methylbenzamide Structure

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N-Methoxy-N-met...

5-Bromo-2-chloroanisole Structure

16817-43-9

5-Bromo-2-chlor...

~53%

(4-chloro-3-methoxyphenyl)-phenylmethanone Structure

834895-50-0

(4-chloro-3-met...

3-Amino-4-chlorobenzoic acid Structure

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3-Amino-4-chlor...

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(3-iodo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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(4-chloro-3-iodophenyl)-phenylmethanone Structure

834895-49-7

(4-chloro-3-iod...

Pyrrolidine Structure

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(3-iodo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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4-Chloro-3-iodo...

~%

(3-iodo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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(3-iodo-4-pyrro...

4-chloro-3-iodobenzoyl chloride Structure

42860-17-3

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~%

(3-iodo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-51-1

(3-iodo-4-pyrro...

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3-Amino-4-chlor...

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(3-bromo-4-pyrr...

(3-bromo-4-chlorophenyl)-phenylmethanone Structure

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(3-bromo-4-chlo...

Pyrrolidine Structure

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834895-52-2

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3-Bromo-4-chlor...

~%

(3-bromo-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-52-2

(3-bromo-4-pyrr...

3-Amino-4-chlorobenzoic acid Structure

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3-Amino-4-chlor...

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4-chloro-3-iodobenzoyl chloride Structure

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4-chloro-3-iodo...

3-Amino-4-chlorobenzoic acid Structure

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Pyrrolidine

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(3,4-dichloroph...

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(3-chloro-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-53-3

(3-chloro-4-pyr...

3,4-Dichlorobenzoic acid Structure

51-44-5

3,4-Dichloroben...

~%

(3-chloro-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-53-3

(3-chloro-4-pyr...

2,3-Dichlorobenzoyl Structure

3024-72-4

2,3-Dichlorobenzoyl

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(3-chloro-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

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(3-chloro-4-pyr...

Pyrrolidine Structure

123-75-1

Pyrrolidine

3-methyl-4-fluoro-benzophenone Structure

345-66-4

3-methyl-4-fluo...

~66%

(3-methyl-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-54-4

(3-methyl-4-pyr...

4-Fluoro-3-methylbenzoic acid Structure

403-15-6

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~%

(3-methyl-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-54-4

(3-methyl-4-pyr...

4-Fluoro-3-methylbenzoyl chloride Structure

455-84-5

4-Fluoro-3-meth...

~%

(3-methyl-4-pyrrolidin-1-ylphenyl)-phenylmethanone Structure

834895-54-4

(3-methyl-4-pyr...


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