wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

0.041 mL

82.15

0.0004

0.811

2.0

 

II

0.031 mL

174.16

0.0002

1.106

1.0

 

III

0.047 mL

260.50

0.0004

2.226

2.0

 

IV

7.0 mL

-

-

 

 

 

V

0.028 g

256.30

0.0001

 

 

(55%)

 

Procedure:  25 mL 1-neck flask, stirbar, septum, N2 inlet

                  Dissolved 0.041 mL of cyclohexene and 0.031 mL of DEAD in 7.0 mL of dry CH2Cl2.  Stirred; cooled to -62 C.  Added 0.047 mL of SnCl4.  After 12 min, the reaction mixture was quenched with water and extracted with CH2Cl2.  The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation.   The product was isolated by flash chromatography on silica gel using 20:80 EtOAc-hexanes as eluant.  The product was a clear, colorless oil.