Comprehensive Organic Functional Group Transformations, Volume 6
A vast range of different functional groups is potentially available from the attachment of three or four heteroatoms to carbon. Some of these are abundantly represented in the literature, others are rare, and many have yet to be described. The aim of this volume is to describe the synthesis of examples of known functional groups and to highlight those that are little known or unknown. All possible combinations of heteroatoms have been surveyed, with the exception of complexes in which carbon atoms are bonded only to transition elements. The material is organised in four parts: tetracoordinated carbon atoms bearing three attached heteroatoms are covered in Part 1, and those bearing four heteroatoms in Part II; the synthesis of tricoordinated carbon
atoms with three attached heteroatoms is described in Part III; stabilized radicals and carbocations with three attached heteroatoms are covered briefly in Part IV.
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Carbon with One Heteroatom Attached by a Single Bond
Ge B or a Metal
Dicoordinate Carbon Functions with Two Doubly Bonded Heteroatoms YCY
Chalcogen or Group 15 Element Also Functions Containing Three Metals
Halogen or Chalcogen
Least One Chalcogen and No Halogen
Chalcogen and No Halogen
Halogen or Chalcogen
Chalcogen or Group 15 Element Also Functions Containing Four Metals
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Abstr acetals acid addition adduct Akad alcohols alkenes alkyl Allg amines analogous Angew anion Anorg aryl bond bromine butyllithium carbon atoms carbon disulfide carbonimidic carbonyl catalyst Chalcogen Chem Chemistry Chim chloride chloroformate complexes compounds corresponding cyclic derivatives dichloride diethyl difluoride dithiocarbamates dithiocarbonate electrophilic Engl esters ether example fluoride Fluorine Chem formation formed Functions bearing FUNCTIONS CONTAINING give GROUP 15 ELEMENT halides halogen heteroatom Heterocycl high yield hydrogen Iminocarbonyl Inorg intermediate iodide isocyanate isothiocyanates Khim lithiated lithium Me2N Metal Function Metalloid method methyl mixture Nauk SSSR nitrogen functions NMe2 nucleophilic Obshch obtained Organomet Organometallics ortho-esters oxidation oxygen Perkin Trans phosgene phosphine phosphorus potassium prepared presence react reaction reagents reported salts Scheme 12 selenium silicon silyl sodium substituted sulfides sulfur synthesis Tetrahedron Lett thiols thiophosgene TMS TMS treatment trichloromethyl trifluoromethyl undergo yield Scheme ylides