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

Journal of the American Chemical Society

Nature of the carbonium ion. X. 2-Protoadamantyl cation

LA Spurlock, KP Clark

Index: Spurlock,L.A.; Clark,K.P. Journal of the American Chemical Society, 1972 , vol. 94, # 15 p. 5349 - 5360

Full Text: HTML

Citation Number: 21

Abstract

Results Bicyclo [3.2. l] oct-6-en-3-one (1) was prepared through the ring expansion of norbornadiene by the methods of Moore, Moser, and La Prade6 and LeBel and Liesemer. 7 Reduction of 1 with a large excess of sodium in ethanol afforded a mixture of exo-and endo- bicyclo [3.2. l] oct-6-en-3-01s (see Scheme I). 8 Analysis of the alcohol mixture by gc showed it to be 95% 2a and 5% of its endo epimer.

bicyclo[3.2.1]oct-6-en-3-one Structure

bicyclo[3.2.1]o...

~%

9-Protoadamantanon Structure

9-Protoadamantanon

Norbornadiene Structure

~%

9-Protoadamantanon Structure

9-Protoadamantanon

exo-Bicyclo[3.2.1]oct-6-en-3-ol Structure

exo-Bicyclo[3.2...

~%

9-Protoadamantanon Structure

9-Protoadamantanon

N/A Structure

~%

9-Protoadamantanon Structure

9-Protoadamantanon

endo-Bicyclo(3.2.1)oct-6-en-3-ylessigsaeure Structure

endo-Bicyclo(3....

~%

9-Protoadamantanon Structure

9-Protoadamantanon

N/A Structure

~%

9-Protoadamantanon Structure

9-Protoadamantanon

N/A Structure

~%

9-Protoadamantanon Structure

9-Protoadamantanon

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

~%

9-Protoadamantanon Structure

9-Protoadamantanon

2-(endo-Bicyclo[3.2.1]oct-6-en-3-yl)ethyl-chlorid Structure

2-(endo-Bicyclo...

~%

9-Protoadamantanon Structure

9-Protoadamantanon

bicyclo[3.2.1]oct-6-en-3-one Structure

bicyclo[3.2.1]o...

~%

7-Protoadamantanon Structure

7-Protoadamantanon

Norbornadiene Structure

~%

7-Protoadamantanon Structure

7-Protoadamantanon

exo-Bicyclo[3.2.1]oct-6-en-3-ol Structure

exo-Bicyclo[3.2...

~%

7-Protoadamantanon Structure

7-Protoadamantanon

N/A Structure

~%

7-Protoadamantanon Structure

7-Protoadamantanon

endo-Bicyclo(3.2.1)oct-6-en-3-ylessigsaeure Structure

endo-Bicyclo(3....

~%

7-Protoadamantanon Structure

7-Protoadamantanon

N/A Structure

~%

7-Protoadamantanon Structure

7-Protoadamantanon

N/A Structure

~%

7-Protoadamantanon Structure

7-Protoadamantanon

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

~%

7-Protoadamantanon Structure

7-Protoadamantanon

2-(endo-Bicyclo[3.2.1]oct-6-en-3-yl)ethyl-chlorid Structure

2-(endo-Bicyclo...

~%

7-Protoadamantanon Structure

7-Protoadamantanon

bicyclo[3.2.1]oct-6-en-3-one Structure

bicyclo[3.2.1]o...

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

Norbornadiene Structure

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

exo-Bicyclo[3.2.1]oct-6-en-3-ol Structure

exo-Bicyclo[3.2...

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

N/A Structure

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

endo-Bicyclo(3.2.1)oct-6-en-3-ylessigsaeure Structure

endo-Bicyclo(3....

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

N/A Structure

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

N/A Structure

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...

Bromoform Structure

Norbornadiene Structure

~%

bicyclo[3.2.1]oct-6-en-3-one Structure

bicyclo[3.2.1]o...

2-(endo-Bicyclo[3.2.1]oct-6-en-3-yl)ethyl-chlorid Structure

2-(endo-Bicyclo...

~%

2,5-Methano-1H-inden-1-one, octahydro Structure

2,5-Methano-1H-...