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Formal addition of diazomethane's terminal nitrogen atom to the 9,10-positions of anthracene yields H 2 CN 2  A ( 1 , A = C 14 H 10 or anthracene). The synthesis of this hydrazone is reported from Carpino's hydrazine H 2 N 2  A through treatment with paraformaldehyde. Compound 1 has been found to be an easy-to-handle solid that does not exhibit dangerous heat or shock sensitivity. Effective umpolung of the diazomethane unit imbues 1 with electrophilicity at the methylene carbon center. Its reactivity with nucleophiles such as H 2 CPPh 3 and N-heterocyclic carbenes is exploited for C[double bond, length as m-dash]C bond formation with elimination of dinitrogen and anthracene. Similarly, 1 is demonstrated to deliver methylene to a nucleophilic singlet d 2 transition metal center, W(ODipp) 4 ( 2 ), to generate the robust methylidene complex [ 2 [double bond, length as m-dash]CH 2 ]. This behavior is contrasted with that of the Wittig reagent H 2 CPPh 3 , a more traditional and Brønsted basic methylene source that upon exposure to 2 contrastingly forms the methylidyne salt [MePPh 3 ][ 2 [triple bond, length as m-dash]CH].

Diazomethane umpolung atop anthracene: an electrophilic methylene transfer reagent