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21st August 2013 @ 13:36

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Reaction information

*#Reaction file  
CSRxnsScheme_130B.cdx
*Reaction file type CDX
*Procedure

 General procedure D (see below) with diene 123j (247 mg, 0.66 mmol) and N‑phenylmaleimide (125 mg, 0.72 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 1:1) gave the title compound as an orange oil (319 mg, 88%). 

 

General procedure D:

The appropriate dienophile (1.1 eq.) was added to diene 123a,c or j (1 eq.) in benzene (1.00 mL).  The reaction mixture was heated at reflux for 16 h.  The solvent was removed in vacuo to give the crude product, which was purified as described.

 

*Yield (%)  88
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp100.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 130b: endo-5,9-Dibutyl-7-phenyl-1-tosyl-3,4,5,5a,8a,9-hexahydro-1H-cyclopenta[g]quinoline-6,8(2H,7H)-dione

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp100.pdf
CSRxnsScheme_130B.cdx
AH Thesis_2011_pp176-223.pdf