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

Journal of the American Chemical Society

Photochemical [3+ 2] cycloaddition reactions of alkynones. Diverse fates of two similar vinylcarbene intermediates and reactions of a cyclopropenol

S Wolff, WC Agosta

Index: Wolff,S.; Agosta,W.C. Journal of the American Chemical Society, 1984 , vol. 106, p. 2363

Full Text: HTML

Citation Number: 15

Abstract

Abstract: Irradiation of alkynone 4 with tetramethylethylene (2) in wet benzene furnishes in high yield the simple cyclopropenol lla. Thermolysis of lla gives the conjugated allenic ketone 5 with loss of C3H6; treatment of lla with sodium hydride leads to 19, and on standing in inert solvent at room temperature lla ejects acetone. In contrast the related alkynone 7 adds 2 photochemically to yield 25, which rearranges at 75 'C to 8. In explanation of the ...

1,3-di-tert-butyl-2-(2-hydroxy-1,1,2-trimethylpropyl)-2-cyclopropen-1-ol Structure

1,3-di-tert-but...

methyl iodide Structure

~20%

4-tert-butyl-2,2,6-trimethylhept-5-en-3-one Structure

4-tert-butyl-2,...

4-tert-butyl-2,2,4,6-tetramethylhept-5-en-3-one Structure

4-tert-butyl-2,...

Detail

3,3-Dimethyl-1-Butyne Structure

3,3-Dimethyl-1-...

~%

2,2,6,6-tetramethylhept-4-yn-3-ol Structure

2,2,6,6-tetrame...

(3,3-dimethylbut-1-yn-1-yl)magnesium bromide Structure

(3,3-dimethylbu...

Pivaldehyde Structure

~%

2,2,6,6-tetramethylhept-4-yn-3-ol Structure

2,2,6,6-tetrame...

3,3-Dimethyl-1-Butyne Structure

3,3-Dimethyl-1-...

~%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

2,2,6,6-tetramethylhept-4-yn-3-ol Structure

2,2,6,6-tetrame...

~%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

(3,3-dimethylbut-1-yn-1-yl)magnesium bromide Structure

(3,3-dimethylbu...

~%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

1,3-di-tert-butyl-2-(2-hydroxy-1,1,2-trimethylpropyl)-2-cyclopropen-1-ol Structure

1,3-di-tert-but...

~15%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

3-(2,3-di-tert-butyl-3-methoxycycloprop-1-en-1-yl)-2,3-dimethylbutan-2-ol Structure

3-(2,3-di-tert-...

~15%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

tetramethylethylene Structure

tetramethylethylene

2,2,6,6-tetramethylhept-4-yn-3-one Structure

2,2,6,6-tetrame...

~64%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

2-(tert-butyl)-2-(3,3-dimethylbut-1-yn-1-yl)-3,3,4,4-tetramethyloxetane Structure

2-(tert-butyl)-...

2,2,6,6-tetramethylhept-4-yn-3-one Structure

2,2,6,6-tetrame...

~%

4-tert-butyl-2,2,6-trimethylhepta-4,5-dien-3-one Structure

4-tert-butyl-2,...

1,3-di-tert-butyl-2-(2-hydroxy-1,1,2-trimethylpropyl)-2-cyclopropen-1-ol Structure

1,3-di-tert-but...

~85%

4-tert-butyl-2,2,6-trimethylhept-5-en-3-one Structure

4-tert-butyl-2,...

1,3-di-tert-butyl-2-(2-hydroxy-1,1,2-trimethylpropyl)-2-cyclopropen-1-ol Structure

1,3-di-tert-but...

methyl iodide Structure

~5%

4-tert-butyl-2,2,6-trimethylhept-5-en-3-one Structure

4-tert-butyl-2,...

4-tert-butyl-2,2,4,6-tetramethylhept-5-en-3-one Structure

4-tert-butyl-2,...

Detail

1,3-di-tert-butyl-2-(2-hydroxy-1,1,2-trimethylpropyl)-2-cyclopropen-1-ol Structure

1,3-di-tert-but...

~83%

4-tert-butyl-2,2,6-trimethylhept-5-en-3-one Structure

4-tert-butyl-2,...

Acetone Structure