Tetrabutylammonium hydrogen bisbenzoate: crystal structure and study of short hydrogen bonds in hydrogen bisbenzoate anion system

Tetrabutylammonium hydrogen bisbenzoate (bioxyanion) is a useful nucleophile, soluble in organic solvents and capable of catalysing the silylketene acetal initiated group transfer polymerisation of alkylacrylate monomers, as well as a carbonate interchange reaction of aromatic biphenols with diphenyl carbonate. Tetrabutylammonium hydrogen bisbenzoate has been characterised by 1H and 13C NMR as well as FTIR spectroscopy and compared with its acid and corresponding salts. The structure of [N(Bu)4]+[(PhCOO)2H]- was determined by single crystal X-ray diffraction. Crystals of C30H47NO4 are orthorhombic, space group Pccn with a= 13.038(1), b= 13.589(1), c= 17.124(3)Å and Z= 4. Half of each cation and anion is related to the other half by a two fold axis parallel to the c axis and nitrogen atoms as well as hydrogen atoms of the O ··· H ··· O group being placed on the two-fold axis. Two benzoate residues in the anion are linked through a short crystallographically symmetrical O ··· H ··· O hydrogen bond with O ··· O distance of 2.459(3)Å. Bifurcated C-H ··· O hydrogen bonds from oxygen of the carbonyls connect the cations and anions to form infinite chain networks in the crystal

Rearrangement of a homobrendane to a perhydro-1,4-methanoindene skeleton. X-ray crystal structure of a novel product

A novel compound obtained by Grignard reaction of the tricyclic hydroxy ketone (1) followed by acid treatment has been assigned structure (3) on the basis of spectral and X-ray crystal structure analyses

Rearrangement of a Homobrendane to a Perhydro-l,4=methanoindene Skeleton. X-Ray Crystal Structure of a Novel Product

A novel compound obtained by Grignard reaction of the tricyclic hydroxy ketone (1) followed by acid treatment has been assigned structure (3) on the basis of spectral and X-ray crystal structure analyses

Novel intramolecular reductive Carbon-carbon coupling during borohydride reduction of dispiro[naphthalene-1,2′2^{\prime}(1′1^{\prime}H)-naphtho[2,1-b]pyran-3′3^{\prime},1^{\prime}^{\prime}-naphthalene]-2(1H),2^{\prime}^{\prime}(1^{\prime}^{\prime}H)-dione and similar dispironaphthalenones

$NaBH_4$ reduction of the title compounds I $(R=H, Br, Me_3C, 1-methyl-1-cyclohexyl)$ gave the coupling products II, III and IV $(R1=Me, Et, Me_2CH)$