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CHEM40211 Organic Synthesis of Compounds

Question

Answered

Task:

1. Reading

All the standard textbooks are useful, but the best coverage is in Clayden, March and the Oxford Chemistry Primer No 5 - ‘Polar Rearrangements’ by L. M. Harwood.

Always look for the driving force of the reaction and be aware of the evidence that tells you about a certain mechanistic pathway, particularly migratory aptitudes or labelling studies.

2. Terminology and basics

1. Classification - As nucleophilic or electrophilic rearrangements, stepwise or concerted.
2. Nature of the migration - Stereochemical implications of concerted or stepwise rearrangements ie racemisation, retention and inversion.Look out for neighbouring group participation and migratory aptitudes of groups depending upon the classification of the rearrangement. 

To carbon
i.  Wagner Meerwein - 1,2 alkyl shifts particularly noting the stereochemical requirements in cyclic systems.
ii.  Nametkin - 1,2 methyl shifts in terpenes.
iii.  Tiffeneau Demyanov - amino alcohol rearrangement with nitrous acid; note use in cyclic ketones for ring expansion and contraction.
iv.  Pinacol - 1,2 diols with acids; similar to above but look for use in preparing spirocyclic systems.
v.  Dienone Phenol - 1,2 alkyl shift where the driving force is aromatisation.
vi.  Hydride Shifts - usually only when steric constraints disfavour alkyl shifts, but note transannular migrations.
vii.  Rearrangements of aldehydes and ketones - acid catalysed, evidence for pathways.
viii.  Non classical carbocations - stereochemical requirements.

Nucleophilic rearrangements to carbon

Base initiated: 

i.  Favorskii -  halo carbonyls; evidence and ring contractions.
ii.  Ramberg Backlund - halo sulphone extrusion of SO2.
iii.  Benzil - benzilic acid - diketones and extension to use with C nucleophiles
iv.  Methylene extension - diazomethane addition to ketones and ring expansion.

Involving carbenes:

Wolff rearrangement - diazoketone rearrangement; use in Arndt - Eistert homologation and carbon chain extension. 

Problems

1. Give mechanisms for the following acid catalysed reactions.
2. Suggest mechanisms for the following rearrangements

CHEM40211 Organic Synthesis of Compounds

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