By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)
This quantity describes all equipment for the synthesis of compounds containing acarbon atom singly bonded to a heteroatom substituent. the amount is prepared in 3 elements facing sp3, sp2 and sp carbon associated with the heteroatoms. for every part cautious awareness has been given to numerous gains reminiscent of substitution styles, ring results, pressure results, neighbouring performance, stereochemistry, and so forth. that can mediate the synthesis pathway. Emphasis has additionally been given to the best and useful coaching of a few of the sensible teams. severe evaluation ofthe techniques permits the reader to choose tools ultimate for his or her wishes. during this quantity the heteroatom can also be metal and for that reason replicate a hugely polarised bonding association with the carbon substituent. Compounds containing unmarried bonds among carbon and heterofunctional teams represent the biggest category and most ordinarily remodeled natural sensible teams.
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Extra resources for Comprehensive Organic Functional Group Transformations, Volume 2 (Synthesis: Carbon with One Heteroatom Attached by a Single Bond)
Free extracts ð83TL3458Ł[ 2! aryl! ketoesters\ are reduced with higher levels of enantio! called Mar! diols ð60CJC1475Ł[ The acid! isomer ð78CC0318Ł as predicted by theoretical studies ð73T1146Ł[ Mes! borabicyclo! diboranes upon reaction with diborane[ These diboranes are con! verted to primary alcohols upon usual peroxidative workup "Scheme 1# ð56JA180Ł[ BR2 2 BH3 H2O2 NaOH BR2 BR2 OH Scheme 2 1[91[0[1[0 Stereo! pinene is a good example of the regio! based Functional Groups seen in such reactions^ the initial product of addition is diisopinocampheylborane "Ipc1BH#\ arising from regio!
Selective ð81TL5396Ł and has been used to synthesise all four isomers of disparlure ð81TL5300Ł[ To accomplish highly selective hydroxylation of a\b! unsaturated amides\ a modi_ed AD! mix employing a _vefold increase in the ligand and potassium osmate is required ð82TL1968Ł[ When this new\ improved mix was used\ both a\b!
Pinene is a good example of the regio! based Functional Groups seen in such reactions^ the initial product of addition is diisopinocampheylborane "Ipc1BH#\ arising from regio! heterocycloalkenes at −14>C to give trans! 1! metal complexes[ The observation that Wilkinson|s catalyst catalysed the addition of catecholborane to alkenes at ambient temperature was _rst made in 0874 ð74AG"E#767Ł^ this observation led workers to examine the reaction of allylic alcohols with the same borane using rhodium catalysis in the expectation that the presence of catalyst would allow a directing e}ect[ Thus the reaction of O!