Sulphinates allyl

Allyl sulphenates, rearrangement of 720-736 Allylsulphenic acids 747 Allyl sulphinates, rearrangement of 670-676 Allylsulphinyipyrazolenines, photolysis of 749... 

Sulphinates 60-70 - see also Alkanesulphinates, Arenesulphinates, Thiosulphinates ally - see Allyl sulphinates chiral - see Chiral sulphinates photolysis of 1076... 

Allyl sulphones can be converted to dienes by alkylation and elimination of sulphinic acid under basic conditions (equation 64)105. Several vitamin A related polyenes have been synthesized following this two-step protocol (Table 10)106. The poor leaving-group ability of the arylsulphonyl group requires treatment with strong base for elimination. However, elimination of the allylsulphonyl group takes place readily under palladium catalysis (equation 65)107. Vinyl sulphones can be converted to dienes via Michael addition, alkylation with allyl halides and elimination of sulphinic acid sequence (equation 66)108. 

Alternatively, the allyl sulphinyl anion (8) gave the threo adduct (9), which underwent sulphoxide - sulphinate ester rearrangement, leading to the hex-2-enitol derivative (10)(Scheme 4) the threo isomer predominated by non-chelation control, which has previously been difficult to achieve. ... 

The photosensitized oxidation of allylthiourea with erythrosin or eosin gave three products, the sulphinic acid (207), allyl cyanamide, and sulphuric... 

CHMel/ thus supporting the interpretation of rearrangements of alkenes in liquid SO 2 that is based on the instability of allyl sulphinic acids. Sodium salts of sulphinic acids take the role of co-catalyst in PdClj-catalysed dimerization of butadiene in an alcohol solvent, leading to octa-2,7-dienyl alkyl ethers, and act as arylating agents towards cyclo-octa-1,5-diene in the presence of PdClj. ... 

Allylic sulphones are available through the reaction of a t-butyl sulphoxide and an allyl alcohol with A -chlorosucdnimide, and through the reaction of an allyl alcohol with di(AT-phthalimido) sulphide or di(iV-imidazolyl) sulphide to give a sulphoxylate, e.g. CHa=CHCH20S0CH2CH=CH2, which rearranges to the bis(allyl) sulphone by way of the sulphinate. Further study of the rearrangement of iV-aryl arenesulphonamides to iV-(u-aminoaryl) aryl sulphones has been described. ... 

---