Transcription of Functional Group Interconversions - Vanderbilt University
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Functional Group Interconversions - Vanderbilt University
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. Halides are less reactive than sulfonate esters, howeverelimination as a competing side reaction is also sulfonate esters can be converted to halides with the sodium halide in acetoneat reflux.
Amides and Lactams - reaction of an "activated acid" with amines - Beckman Rearrangement Organic Reactions 1988, 35, 1 R R' O R R' N OH R NR' PCl 5 O - Schmidt rearrangement R R' O HN 3 H+ R NR' O - others OTf O NR 2 CO, DMF Pd(0), R 2NH TL 1985, 26, 1109 OTHP O O PhCH 2NH 2 AlMe 3 OTHP OH N H Ph O TL 1977, 4171-Weinreb amide Tetrahedron Lett ...
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