Dolbier HW Solutions 473

Dolbier HW Solutions 473 - CCl O p-Methoxybenzoyl chloride...

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both Grignard functions of the reagent attack the lactone. The second attack is intramolecu- lar, giving rise to the cyclopentanol ring of the product. ( b ) An intramolecular acyl transfer process takes place in this reaction. The amine group in the thiolactone starting material replaces sulfur on the acyl group to form a lactam (cyclic amide). 20.37 ( a ) Acyl chlorides react with alcohols to form esters. 1 pyridine CCH O OH Benzoin CH 3 O
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Unformatted text preview: CCl O p-Methoxybenzoyl chloride CCH O O C OCH 3 O Benzoin p-methoxybenzoate (compound A; 95%) O N H HS Lactam S OH NH Tetrahedral intermediate S NH 2 O Thiolactone 1 4-Butanolide 1-(3-Hydroxypropyl)-cyclopentanol (88%) O O 1 BrMg CH 2 CH 2 CH 2 CH 2 MgBr O CH 2 MgBr 2 O O CH 2 MgBr 1 O BrMg 1 2 O BrMg 1 2 O MgBr 1 2 HO OH H 3 O 1 2 2 CARBOXYLIC ACID DERIVATIVES: NUCLEOPHILIC ACYL SUBSTITUTION 567...
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This note was uploaded on 09/30/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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