Friday_Session_2_solution

Friday_Session_2_solution - Chem 358 Spring 2009 Friday...

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Unformatted text preview: Chem 358 Spring 2009 Friday Session 2 – Solutions (Answer 4(d) corrected) 1. ( A) NH 2 CN Br Br O Stille or Gilman or Suzuki Friedel-Crafts Acylation Proposed forward synthesis Br 2 FeCl 3 Br (CH 3 CH 2 ) 4 Sn Pd(PPh 3 ) 4 NBS Peroxide Br NaCN CN NH 2 H 2 Pt (B) Retrosynthesis Br O + Cl O Br + H H Br CuLi 2 + Gilman Heck or Stille Proposed forward synthesis + Cl O AlCl 3 O Na[Hg], HCl, ! NBS Peroxide Br 1. t-BuOK 2. H 3 O + OR Br 2 FeCl 3 Br H H Pd(PPh 3 ) 4 , Et 3 N SnBu 3 Pd(PPh 3 ) 4 CuLi 2 ———————————————————————————————————————————— (C) Retrosynthesis Br + Sn 4 + Br Br + CuLi 2 Gilman Stille Friedel-Crafts Proposed forward synthesis Br 2 FeCl 3 Br Sn 4 Pd(PPh 3 ) 4 CuLi 2 Br 1. , FeBr 3 2. H 2 , Pt O Cl O AlCl 3 H 2 NNH 2 , HO — , ! ———————————————————————————————————————————— (D) Retrosynthesis Br + CuLi 2 Br + B O O O + Cl O Acylation Gilman Suzuki Proposed forward synthesis Br 2 FeCl 3 Br Sn 4 Pd(PPh 3 ) 4 CuLi 2 O Cl O AlCl 3 H 2 NNH 2 , HO — , !...
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell.

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Friday_Session_2_solution - Chem 358 Spring 2009 Friday...

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