Application of 5-lithiotetrazoles in organic synthesis

Influence of Metal Dilution on the Light‐Induced Spin Transition in Two 1D Chain Compounds: [FexZn1–x(btzp)3](BF4)2 and [FexZn1–x(endi)3](BF4)2 {btzp = 1,2‐Bis(tetrazol‐1‐yl)propane and endi = 1,2‐Bis(tetrazol‐1‐yl)ethane}

“…[11,12] Materials: The ligand [btzp] was prepared from sodium azide, triethyl orthoformate and 1,2-diaminopropane according to the general method described by Kamiya and Saito. [24] The ligand 1,2-(tetrazol-1-yl)ethane [endi] was prepared in a similar method to that used by Satoh et al [25] The preparation of the pure compounds [Fe(btzp) 2 ](BF 4 ) 2 and [Fe(endi) 2 ](BF 4 ) 2 has been described earlier by Gutlich et al [11] and Linert et al [12] The diluted compounds [Fe x Zn 1-x ] were synthesised according to the same procedures, replacing the iron(II) tetrafluoroborate by mixtures of iron(II) and zinc(II) in a given ratio. Iron fraction (x) values were calculated from the iron and zinc atomic percentage determined by quantitative analysis.…”

A Synthon for the Convenient and Efficient Introduction of Tetrazolylmethyl Groups into Nucleophile‐Bearing Compounds

“…[13] Other research teams similarly observed that the debenzylation of tetrazoles requires excessive amounts of palladium catalyst. [21,[30][31][32] Surfraz et al, who tried to deprotect aminocyclitols bearing two benzylated secondary alcohol groups, noticed that the presence of a secondary or tertiary nitrogen atom prevented hydrogenolysis altogether (0 % yield) whereas its absence allowed smooth deprotection under truly catalytic conditions (quantitative yield)! [33] The report by Sajiki and Hirota, [29] that the poisoning effect of nitrogen bases can be repressed by the presence of strong acids, prompted us to investigate the effect of trifluoroacetic acid (TFA) on the deprotection of 2 ( Table 1).…”

Five‐Membered Heterocycles with Four Heteroatoms: Tetrazoles

“…1-Benzyltetrazoles or 1-(para methoxybenzyl)tetrazoles have been regioselectively lithiated at the 5-position using nBuLi in TMEDA/THFat À98 C (Scheme 15.28) [50].…”

“…Scheme 15.28 Electrophilic addition to tetrazoles [50]. Oxidation of the commercially available sodium salt of ethyl-tetrazole-5-carboxylate using oxone in aqueous acetone at pH 7.5 forms, exclusively, N-2-hydroxytetrazole-5-carboxylate (49) (Scheme 15.30) [52].…”