The Double Functional Group Transformation Terminally Unsaturated

The Double Functional Group Transformation Terminally Unsaturated Nitriles from 1-Nitrocydoalkenes 

There is much current interest in the design and development of the double functional group transformation concept, an excellent illustration of which is the now well known and widely exploited Eschenmoser fragmentation reaction. A recent example of the double functional group transformation is the one-flask conversion of 1-nitrocycloalkenes into terminally unsaturated nitriles by treatment first with trimethylsilylmethylmagnesium chloride (1.8 eq.) in THF at -20°C and then, in situ, with PCI3 (2.5 eq.) at 67°C. 2-Nitrobicyclo[2.2.1]hept-2-ene, for example, gave cis-1 -cyano-3-vinylcyclopentane in 33% yield, and similar yields of ene-nitriles were obtained from a variety of monocyclic and bicyclic 1-nitrocycloalkenes. 

Suggest a mechanism for this double functional group transformation . 

Lewis Acid-Catalysed Condensation of Indole with 1,3-Cyclohexanedione 

Addition of freshly distilled BF3,OEt2 to a solution of indole and 1,3-cyclohexanedione in methylene chloride at 0°C gave a mixture of 1 and 2 in 55 and 20% yield respectively. 

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