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Functional Group Interconversions

Functional Group Interconversions 119 Functional Group InterconversionsC&S Chapter 3 #1; 2; 4a,b, e; 5a, b, d; 6a,b,c,d; 81sulfonates2halides3nitriles4azides5ami nes6esters and lactones7amides and lactamsSulfonate Esters- reaction of an alcohols (1 or 2 ) with a sulfonyl chlorideROHROSOOR'CH3CF3CH3R'SO2 Clsulfonate esterR'=mesylatetriflatetosylate- sulfonate esters are very good leaving groups. Elimination is often acompeting side reactionHalides- halides are good leaving groups with the order of reactivity in SN2 reactionsbeing I>Br>Cl.

FUNCTIONAL GROUP INTERCONVERSIONS 124 CO 2 H Pd(OAc) 2 (5 mol %) DMSO, air (86%) O O JOC 1993, 58, 5298 - Selenolactonization OH O O O PhSe O O PhSeCl, CH 2Cl 2 H 2O 2 JACS 1985, 107, 1148 - Mitsunobu Reaction Synthesis 1981, 1; Organic Reactions, 1991, 42, 335 Mechanism: JACS 1988, 110, 6487 R R'

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