e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Photochemical transformations of protonated phenols. A one-step synthesis of umbellulone from thymol

P Baeckstroem, U Jacobsson, B Koutek…

Index: Baeckstroem, Peter; Jacobsson, Ulla; Koutek, Bohumir; Norin, Torbjoern Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3728 - 3732

Full Text: HTML

Citation Number: 18

Abstract

UV irradiation of thymol (7) at 254 or 300 nm in trifluoromethanesulfonic acid affords ten products, eight of which have been isolated and characterized. Four competitive processes are suggested to be operating in the formation of the photoproducts:(i) regioselective type A rearrangement leading to umbellulone (8, about lo%),(ii) formal C2-C3 migration by type A rearrangement and ring opening which affords the principal product, 3-isopropyl-5- ...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~5%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Thymol Structure

~5%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Piperitenone Structure

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~12%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~12%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~11%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~12%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~11%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Thymol Structure

~10%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~10%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~10%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~9%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~10%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Piperitenone Structure

Detail

Phenol,2,3,5,6-tetramethyl- Structure

Phenol,2,3,5,6-...

~6%

2,3,4,6-tetramethylphenol Structure

2,3,4,6-tetrame...

1-Hydroxy-2,3,4,5-tetramethylbenzene Structure

1-Hydroxy-2,3,4...

1,3,4,5-Tetramethylbicyclo[3.1.0]hex-3-ene-2-one Structure

1,3,4,5-Tetrame...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~1%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Thymol Structure

~3%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Phenol,2,3,5,6-tetramethyl- Structure

Phenol,2,3,5,6-...

~15%

2,3,4,6-tetramethylphenol Structure

2,3,4,6-tetrame...

1-Hydroxy-2,3,4,5-tetramethylbenzene Structure

1-Hydroxy-2,3,4...

1,3,4,5-Tetramethylbicyclo[3.1.0]hex-3-ene-2-one Structure

1,3,4,5-Tetrame...

Thymol Structure

~8%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~9%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~8%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~8%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

Thymol Structure

~9%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Piperitenone Structure

Detail

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

~1%

Thymol Structure

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Detail

Thymol Structure

~2%

4-methyl-3,5-di(propan-2-yl)phenol Structure

4-methyl-3,5-di...

3-Isopropyl-5-methylphenol Structure

3-Isopropyl-5-m...

Bicyclo[3.1.0]hex-3-en-2-one,4-methyl-1-(1-methylethyl)- Structure

Bicyclo[3.1.0]h...

Detail

α′-HYDROXY-α, β-UNSATURATED TOSYLHYDRAZONES: PREPARATION AND...

[Baptistella, Lucia H. B.; Aleixo, Adriana M. Synthetic Communications, 2002 , vol. 32, # 19 p. 2937 - 2950]

Tert-Butyl hydroperoxide-pyridinium dichromate: a convenient...

[Chidambaram, Nallaperumal; Chandrasekaran, Srinivasan Journal of Organic Chemistry, 1987 , vol. 52, # 22 p. 5048 - 5051]

Synthesis of terpenes containing the bicyclo [3.1. 1] heptan...

[Kulkarni, Yashwant S.; Niwa, Maho; Ron, Eyal; Snider, Barry B. Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1568 - 1576]

Synthesis of terpenes containing the bicyclo [3.1. 1] heptan...

[Kulkarni, Yashwant S.; Niwa, Maho; Ron, Eyal; Snider, Barry B. Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1568 - 1576]

Regiospecific functionalization of the monoterpene ether 1, ...

[Boggiatto, Margarita V. de; Heluani, Carola S. de; Fenik, Ines J. S.; Catalan, Cesar A. N. Journal of Organic Chemistry, 1987 , vol. 52, # 8 p. 1505 - 1511]