Katritzky A.R., Meth-Cohn O., Rees C.W. Comprehensive Organic Functional Group Transformations. Volume 1. Synthesis: Carbon with No Attached Heteroatoms

Pergamon, 1995. — 1316 p.Comprehensive Organic Functional Group Transformations (COFGT) aims to present the vast subject of organic synthesis in terms of the introduction and interconversion of functional groups.
All organic structures can be considered as skeletal frameworks of carbon atoms to which functional groups are attached; it is the latter which are mainly responsible for chemical reactivity and which are highlighted in COFGT. All known functional groups fit a logical and comprehensive pattern and this forms the basis for the detailed list of contents. The format of the present work was designed with the intention to cover systematically all the possible arrangements of atoms around a carbon, including those which are quite unfamiliar. The work also considers the possibility of as yet unknown functional groups which may be constructed in the future and prove to be important; thus COFGT also indicates what is not known and so points the way to new research areas.
The philosophy of the present work has been to rationalize this enormous subject within as logical and formal a framework as possible, in a scholarly and critical fashion. COFGT is designed to provide the first point of entry to the literature for synthetic organic chemists, together with an unrivalled source for anyone interested in less common, obscure, or unknown functional groups. All functional groups are viewed as being carbon based (even if the group contains no carbon). Thus, a nitro compound is considered from the standpoint of the immediately attached carbon atom, whether di- (sp), tri- (sp²), or tetracoordinated(sp³). The work is organized on the basis of formation or rupture of bonds to a carbon atom and it is the nature of the carbon atom left after the transformation that determines the classification of the overall sequence. Several key criteria have been used to organize the work and to minimize overlap. These are, in order of priority:
the number of attached heteroatoms;
the coordination of the carbon atom involved in the functional group;
the nature of the immediately attached heteroatom(s); and
the Latest Placement Principle.
These four key principles have been used to determine the content of each volume, and to develop
the detailed chapter breakdown within each volume.Tetracoordinated Carbon with No Attached Heteroatoms
One or More CH Bond(s) Formed by Substitution: Reduction of C-Halogen and C-Chalcogen Bonds, One or More CH Bond(s) Formed by Substitution: Reduction of Carbon–Nitrogen, –Phosphorus, –Arsenic, –Antimony, –Bismuth, –Carbon, –Silicon, –Germanium, –Boron, and –Metal Bonds
Two or More CH Bond(s) Formed by Addition to CC Multiple Bonds
One or More CC Bond(s) Formed by Substitution: Substitution of Halogen
One or More CC Bond(s) Formed by Substitution: Substitution of Chalcogen
One or More CC Bond(s) Formed by Substitution: Substitution of Carbon-Nitrogen, –Phosphorus, –Arsenic, –Antimony, –Boron, –Silicon, –Germanium and –Metal Functions
One or More CC Bond(s) Formed by Addition: Addition of Carbon Radicals and Electrocyclic Additions to CC Multiple Bonds
One or More CH and/or CC Bond(s) Formed by Rearrangement
Tricoordinated Carbon with No Attached Heteroatoms
One or More =CH Bond(s) Formed by Substitution or Addition
One or More =CC Bond(s) Formed by Substitution or Addition
One or More C=C Bond(s) Formed by Addition
One or More C=C Bond(s) by Elimination of Hydrogen, Carbon, Halogen or Oxygen Functions
One or More C=C Bond(s) by Elimination of S, Se, Te, N, P, As, Sb, Bi, Si, Ge, B or Metal Functions
One or More C=C Bond(s) Formed by Condensation: Condensation of Nonheteroatom Linked Functions, Halides, Chalcogen or Nitrogen Functions
One or More C=C Bond(s) Formed by Condensation: Condensation of P, As, Sb, Bi, Si or Metal Functions
One or More C=C Bond(s) by Pericyclic Processes
One or More =CH, =CC, and/or C=C Bonds Formed by Rearrangement
Tricoordinate Anions, Cations, and Radicals
Dicoordinate and Monocoordinate Carbon with No Attached Heteroatoms
Allenes and Cumulenes
Alkynes
Ions, Radicals, Carbenes and Other Monocoordinated Systems
References to Volume 1