6214-15-9Relevant articles and documents
CONFORMATIONAL STUDIES OF 7-MEMBERED CYCLIC SULFITES. 3-OXO-2,4,3-DIOXATHIEPIN AND 3-OXO-2,4,3-BENZODIOXATHIEPIN
Faucher, H.,Guimaraes, A. C.,Robert, J. B.,Sauriol, F.,St-Jacques, M.
, p. 689 - 701 (1981)
The conformational and dynamic properties of the 7-membered cyclic sulfites 1 and 2 were investigated by (1)H and (13)C DNMR as well as by IR spectroscopy.Compound 1 showed two spectral modifications at low temperature for both (1)H (100 MHz) and (13)C (22.6 MHz) spectra while for compound 2 a single (1)H spectral change has been observed and resolved at 300 MHz.Analysis of the low temperature NMR spectra together with the IR frequencies for the stretching vibration of the S=O bond indicate that 1 exists as a 1:1 mixture of C-a and TB conformations in CHF2Cl.Less polar solvents increase the proportion of the C-a form.In contrast, compound 2 is found to exist very predominantly as the TB form in CHF2Cl at -160 deg, whereas in the less polar CCl4 solvent a small amount of C-a form is found to be present at room temperature from the IR data.The conformational and dynamic properties determined for 1 and 2 are discussed in light of current theories relating to n -> ?* stereoelectronic lone pair donation and dipole-dipole interactions.Furthermore the results for 1 and 2 are used as the basis for a new conformational interpretation of published IR data for dimethyl sulfite.Finally, the differences in properties of 1 and 2 are discussed.
Thionyl chloride-benzotriazole in methylene chloride: A convenient solution for conversion of alcohols and carboxylic acids expeditiously into alkyl chlorides and acid chlorides by simple titration
Chaudhari, Sachin S.,Akamanchi, Krishnacharya G.
, p. 1763 - 1765 (2007/10/03)
A solution of 1:1 equivalent of thionyl chloride and benzotriazole in dry methylene chloride efficiently transforms alcohols and carboxylic acids into the corresponding alkyl chlorides and acid chlorides respectively at room temperature, with excellent yields by simple titration.
Unsaturated Cyclic Sulfites. I. Synthesis and Condensation with Terminal Acetylene
Kochev, D. M.,Myagkova, G. I.
, p. 700 - 701 (2007/10/03)
Cyclic unsaturated sulfite Δ5-1,3-dioxa-2-thialepin-2-oxide synthesized from (Z)-2-butene-1,4-diol was studied in the condensation with 1-heptyne.The direction of the reaction strongly depends on the conditions.The reaction resulted in (Z)/(E)-2-undecene-5-yn-1-ol and a by-product, 3-(hydroxymethyl)-1-decene-4-yne. - Key words: cyclic unsaturated sulfite; Δ5-1,3-dioxa-2-thialepin-2-oxide; (Z)-2-butene-1,4-diol; (Z)-2-undecene-5-yn-1-ol; (E)-2-undecene-5-yn-1-ol