D -sultones

After a residence time of 15-20 min at a slightly elevated temperature (35°C), the jS-sultones have virtually disappeared and the D-sultones are only present... 

MR Harnden, RL Jarret, MR Boyed, D Sulton, RA Vene Hodge. Prodrugs of the selective antiherpesvirus agent 9-[4-hydroxy-3-(hydroxymethyl) but 1-yl] guanine (BRL 39123) with improved gastrointestinal absorption properties. J Med Chem 32 1738-1743, 1989. 

Table 8 Hydrolysis rates of C and D sultones at various lemperatur C sultones (1,3) (Gamma sultones) hydrolysis rates...

FIG. 3 GC analysis of methyl esters of C14/C16 a-olefin sulfonate mixture. Peak assignments A, methyl 3-tetradecene sulfonate B, sultone from dehydration of tetradecane hydroxysulfonate C, methyl 3-hexadecene sulfonate D, sultone from dehydration of hexade-cane hydroxysulfonate. (Reprinted with permission from Ref. 7. Copyright 1995 by Karl Hanser Verlag.)... 

Neutralization of the sulfonation product from a-olefins is more complex than neutralization of the corresponding products of alkylbenzenes. This is because the S03-a-olefin acid product contains about 50% free sulfonic acid, the rest being C(l,3) and D(l,4) sultones, assuming that with acid aging the 0(1,2) sultones have disappeared. In the case of a-olefins an excess of caustic (1.5-2.0% excess) must be added to neutralize both the sulfonic acid initially present and that formed on subsequent hydrolysis of the C(l,3) and D(l,4) sultones. The sultones (ring-structured esters) cannot be converted to their proper salts by a simple neutralization but need a hydrolysis step. 

Doak, S.M., Simpson, B.J., Hunt, P.F. Stevenson, D.E. (1976) The carcinogenic response in mice to the topical application of propane sultone to the skin. Toxicology, 6, 139-154... 

CH2OH and the sultone F5S d)FCF20 02 265). Mechanistically, the sodium fluoride, the alcohol, or both serve as a catalyst for the rearrangement of the sultone (265,266). The esters formed in this fashion are stable in the presence of F ion at ambient or higher temperatures. The spectral data (IR H, 19F, and 13C NMR and mass) for these... 

Roberts, D.W. and Williams, D.L. (1982) The derivation of quantitative correlations between skin sensitisation and physico-chemical parameters for alkylating agents and their application to experimental data for sultones. f Theor. Biol, 99, 807-825. 

Matonic acid derivatives have been widely used to synthesize fused pyran-2-ones from 2-hydroxyacetophenones [3337]. The uses of cyanoacetamide have been reviewed [3114], An interesting alternative to these malonic acid-based reagents is diphenyl sulphoacetate (29.5a) which reacts in a mildly basic environment. Variations (29.5b-d) on its structure (see table) have been studied and some of these lead to sultones (29.6) instead of coumarins [2741]. 

Xlll 1MPT,XIV Siilpholane, XV - Tctrahydrothiopb.ene-l-oxide, XVI - 1,4-Butanc sultone, XV ll - 2,6-Litidine-A-oxide, XVlll - 2.2,6,6-Tetramethyl-4-pipcridone-1 -oxy d. 

Propane sultone Formula CsHgOsS CAS 1120-71-4 RTECS RP5425000 IDLH Ca [N.D.]... 

I D , Nation 117 I Dgxp, Nation 117 D , 65% sultonated PEEKK Dexp. 65% sultonated PEEKK... 

Peanutamide MIPA Pentadecyl alcohol 1,3-Propane sultone Ricinoleic acid 4-(2-Su Ifoethy I )-pyri d i ne... 

The hydrolysis reaction of C(l,3) and D(l,4) sultones can be described as pseudo first order in the conversion of sultones ... 

The combination of neutralisation/hydrolysis gives a product containing about 55-65% alkene sulphonates and 25-35% hydroxy alkane sulphonates and 5-15% disulphonates. The C(l,3) sultones and D(l,4) sultones have virtually disappeared in the plug flow reactor with a residence time of 30 minutes at HO C. The ratio between initial and final concentration of delta (1,4) sultones will be ... 

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