By S.L. Schreiber
Quantity 1 presents an in depth survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl performance. Emphasis has been put on these reagents that lead to hugely selective addition reactions. tools are said to choose, for instance, one carbonyl crew over one other within the comparable molecule, or so as to add preferentially a fraction to 1 (enantiotopic of diastereotopic) face of a carbonyl workforce. procedures that consequence from an preliminary addition to the C=X sensible crew, for instance alkenations and rearrangements, also are coated during this quantity.
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Extra resources for Additions to C-X &pgr;-Bonds, Part 1, Volume 1
Reaction of the pioduct (200) with diethylethylenediamine and carbonyldiimidazole results in transfer of the C D I nirbonyl group and formation of the urea s u r i c a i n i d e (201) . T h e transform in all likelihood involves stepwise replacement of the imidazole groups by the basic groups in the other reactants. Monocyclic Aromatic Compounds 50 -SO2CH2CH2C1 + H2NCHMe2 •SO2CH2CH2NHCHMe2 (200) (199) Et2NCH2CH2NH2 o II - SO2CH2CH2NCNHCH2CH2NEt2 A Me Me (201) The antiparasitic drug clorsulon (206), contains a rather unusual trichloroethylene group.
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Monocyclic Aromatic Compounds 28 r - OCH2CHCH2NHCHMe2 —*~ MeOCCH^CHf(48); R - H (49); R = Me (50) Inclusion of one of the phenolic groups present in epinephrine in a compound which otherwise looks like a classic beta blocker, leads to an agent which displays agonist rather than antagonist activity . This agent xamoterol (55) can, in principle, be prepared by a convergent synthesis which starts by reaction of the chloroformamide of morpholine (51) with ethylenediamine to give 52. Reaction of a singly protected derivative of hydroquinone (53) with epichlorohydrin will give epoxide 54.