Flowchart for classification of reactions
- Are any bonds involved other than those in protection or deprotection?
- N: PROTECTION or DEPROTECTION
- Y: 2
- Is a polymer formed?
- N: 3
- Y: POLYMERISATION
- Is at least one ring necessarily formed, expanded, or contracted?
- N: 8
- Y: 4
- Is a fused ring system necessarily created (incl. when resulting from changes to existing rings)?
- N: 5
- Y: FUSED-RING SYSTEM FORMATION
- Does the number of rings in the molecule increase?
- N: 6
- Y: RING FORMATION
- Is the product the result of breaking one ring and then forming another elsewhere, or vice versa?
- N: 7
- Y: RING REARRANGEMENT
- Is an existing ring expanded?
- N: RING CONTRACTION
- Y: RING EXPANSION
- Is at least one skeletal ring necessarily broken?
- N: 9
- Y: RING-BREAKING
- Is there a change in the number of atoms in the skeleton?
- N: 20
- Y: 10
- Is there an increase in the number of atoms in the skeleton?
- N: 17
- Y: 11
- Does the reaction involve the redistribution of two multiple bonds among two fragments in a four-centred metallacyclic intermediate?
- N: 12
- Y: MULTIPLE-BOND METATHESIS
- Is a single carbon atom added to the end of a chain?
- N: 13
- Y: END-OF-CHAIN HOMOLOGATION
- Are one or more atoms added in the middle of a chain?
- N: 14
- Y: INSERTION
- Does a rearrangement take place?
- N: 15
- Y: JOINING WITH REARRANGEMENT
- Does the increase in number of skeletal atoms result from the formation of just one (single or multiple) carbon-carbon bond?
- N: SKELETON JOINING
- Y: 16
- Does the reaction necessarily involve the joining of two identical components to form a symmetrical product?
- N: CARBON-CARBON COUPLING
- Y: CARBON-CARBON HOMOCOUPLING
- Is a single skeletal carbon atom removed from the end of a chain?
- N: 18
- Y: END-OF-CHAIN CHAIN SHORTENING
- Are skeletal atoms removed from the middle of a chain, with the two parts of the skeleton re-joining in the product?
- N: 19
- Y: EXTRUSION
- Is the skeleton split into three or more fragments?
- N: CLEAVING
- Y: FRAGMENTATION
- Does the molecule rearrange so that one or more atoms move from one atom to another?
- N: 21
- Y: REARRANGEMENT
- Are there any changes to the bond orders of the bonds between skeletal atoms?
- N: 23
- Y: 22
- Are two or more groups of atoms removed from the molecule, resulting in a change of bond order?
- N: ADDITION
- Y: ELIMINATION
- Does just one functional group undergo a change?
- N: 24
- Y: FUNCTIONAL-GROUP MODIFICATION
- Is the functional group displaced by one or more H atoms?
- N: 25
- Y: FUNCTIONAL-GROUP REDUCTION
- Is one singly-bonded substituent replaced by another singly-bonded substituent?
- N: 26
- Y: SUBSTITUTION
- Are at least some of the atoms of the functional group retained during the reaction?
- N: 27
- Y: FUNCTIONAL-GROUP MODIFICATION
- Is the functional group oxidised?
- N: FUNCTIONAL-GROUP REDUCTION
- Y: FUNCTIONAL-GROUP OXIDATION
Version 11 DJB 10th Oct 2008