chap10f.pptVIP

* TOSYLATES The material here is from Chap. 12 and is repeated in Chap. 12 slides. p-TOLUENESULFONYL CHLORIDE TOSYLATE ESTER + pyridine TOSYLATES ALCOHOL + TsCl ROTs TOSYL CHLORIDE TsCl R-OTs Good leaving group for both SN1 and SN2 .. : .. pyridine + .. CONVERSION TO A TOSYLATE WITH TsCl AND PYRIDINE Poor leaving group Cl - Cl - + * * If the alcohol is chiral, the conversion to a tosylate retains configuration. CH3-CH-OH Ph CH3-CH-OTs Ph TsCl pyridine (R) (R) NaCN acetone CH3-CH-CN Ph (S) RETENTION INVERSION SN2 EXAMPLE OF THE USE OF A TOSYLATE .. NaCN acetone pyridine The first reaction step