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Parnell, Edgar William (1960) Synthetic applications of acrtylonitrile and related compounds. Doctoral thesis, Sir John Cass College.
The preparation of 1-[2-methylcyclohex-1-enyl]butan-3-one (XIIIa, page 14), and attempts to cyclise it to 2-oxo-9-methyl-decalin are described.
The use of acrylonitrile in the synthesis of some derivatives of 2-naphthalenone has been investigated and a new synthesis of some 1-substituted 2-oxo-∆1 (9)-octalins has been achieved.
Acrylonitrile has been used to prepare 10-methyldeca-hydroquinoline (XXXVIII, page 33), octahydropyrindine (LVII, page 42), and cyclohepta[b]piperidine (LXIII, page 46) in both the cis- and trans- forms by stereospecific syntheses.
The preparation of 3-[2-hydroxy-2-methylcyclohexyl]-propylamine (XLVI, page 36) and its cyclisation to 9-methyldecalydroquinoline (XLV, page 36) are described.
The reactions of acrylonitrile with benzaldehyde in the presence of water, methanol, piperidine, and 2-nitropropane have been examined, and the structures of the products elucidated.
Ethyl phenylacetate has been reacted with acrylonitrile and shewn to give a monocyanoethyl derivative.
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