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A molecular rearrangement is described that demonstrates how alkyl-metal-carbenes are generated when metal derivatives combine with acetylenes and olefins and shows that tungsten-carbenes not stabilized by heteroatoms insert into acetylenes. It reveals that this insertion can be remarkably stereo-selective. With catalytic amounts of carbene-tungsten carbonyls, biphenyls substituted at the 2 and 2' positions by vinyl and acetylene groups yield isomeric 9-vinylphenanthrenes. With stoichiometric amounts, they yield 9-vinyl-phenanthrenes whose structures contain the carbene moiety of the metal-carbene. (Author)
Katz et al. (Fri,) studied this question.