New PDF release: Comprehensive Organic Functional Group Transformations,

By Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)

ISBN-10: 008042323X

ISBN-13: 9780080423234

This quantity describes all tools 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 recognition has been given to numerous positive factors akin to substitution styles, ring results, pressure results, neighbouring performance, stereochemistry, and so on. which may mediate the synthesis pathway. Emphasis has additionally been given to the best and functional guidance of many of the practical teams. serious evaluation ofthe tactics permits the reader to pick equipment just right for his or her wishes. during this quantity the heteroatom can also be steel and as a result mirror a hugely polarised bonding association with the carbon substituent. Compounds containing unmarried bonds among carbon and heterofunctional teams represent the most important type and most typically 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)

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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!

Bination with either I1:CuO = HBF3 ð76CC0380\ 89JCS"P0#1796Ł or the stable solid reagent bis"pyr! transfer catalysts ð71TL3540\ 78JCR"S#093\ 81JCS"P0#1298Ł[ Alter! 90Ł[ 1[90[3[3 Alkyl Bromides from Alcohols and their Derivatives A number of methods for the conversion of alcohols to halides "including bromides# have already been discussed in Section 1[90[0[3[0[ As is the case with the other halides\ conversion of alcohols to alkyl bromides using HBr works well "particularly in systems where the SN0 pathway is facilitated by stabilisation of the intermediate carbocation ð30OSC"0#14\ 76JOC4459Ł\ but rearrangements of the carbonium ion sometimes occur[ While the use of phase transfer catalysis can reduce rearrangements considerably ð76TL0112Ł\ and has even facilitated the preparation of primary bromides using HBr ð76JCS"P0#1046Ł\ a far more popular reagent\ which also leads to less rearrangement\ is phosphorus tribromide\ PBr2[ Although PBr2 can be generated in situ from phosphorus and bromine ð30OSC"0#25\ 32OSC"1#297Ł\ it is more common to use commercially available liquid PBr2 ð32OSC"1#247Ł[ The presence of pyridine can help ð44OSC"2#682Ł\ or the PBr2 can be conveniently adsorbed onto a resin!

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!

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Comprehensive Organic Functional Group Transformations, Volume 2 (Synthesis: Carbon with One Heteroatom Attached by a Single Bond) by Alan R. Katritzky, Otto Meth-Cohn, and Charles W. Rees (Editors-in-Chief)


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