Effect of gem 2,2′-disubstitution and base in the formation of spiro- and ansa-1,3-propandioxy derivatives of cyclotriphosphazenes was written by Uslu, Aylin;Coles, Simon J.;Davies, David B.;Esen, Muekremin;Hursthouse, Michael B.;Kilic, Adem. And the article was included in Inorganica Chimica Acta in 2010.Formula: C9H20O2 The following contents are mentioned in the article:
The gem-dialkyl effect was studied in the reactions of cyclotriphosphazene, N3P3Cl6 1, with various 2,2′-derivatives of 1,3-propandiol, CXY(CH2OH)2, in either THF or DCM to form spiro (6-membered) and ansa (8-membered ring) derivatives The reactions were made with a number of sym.-substituted (X = Y, Me, Et, Bu and a malonate ester) and unsym.-substituted (X ≠ Y, Me/H, Ph/H, Me/Pr, Et/Bu and Br/NO2) 1,3-propandiols. The products were analyzed by 1H and 31P NMR spectroscopy and some of the spiro and ansa derivatives were also characterized by x-ray crystallog. Reactions of 1 with unsym.-substituted 1,3-propandiols gave two structural isomers of ansa-substituted compounds, both isomers (endo and exo) were structurally-characterized by x-ray crystallog. for the Et/Bu derivative The regioselectivity of the reaction is changed when the base is changed. The relative proportions of spiro and ansa compounds formed under different reaction conditions were quantified by 31P NMR measurements of the reaction mixtures The results were rationalized mainly in terms of the electronic effect of the substituents, whereas the steric effect has a secondary role in the formation of both spiro and ansa compounds This study involved multiple reactions and reactants, such as 2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4Formula: C9H20O2).
2-Butyl-2-ethylpropane-1,3-diol (cas: 115-84-4) belongs to alcohols. Alcohols are among the most common organic compounds. They are used as sweeteners and in making perfumes, are valuable intermediates in the synthesis of other compounds, and are among the most abundantly produced organic chemicals in industry. Secondary alcohols are easily oxidized without breaking carbon-carbon bonds only as far as the ketone stage. No further oxidation is seen except under very stringent conditions.Formula: C9H20O2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts