Allyltriphenylphosphonium bromide

Allyl alcohol Allyl bromide Allyltriphenylphosphonium bromide... 

Non-gelatinizing phosphonium starch ethers were obtained by treating starch with 2-chloroethyltributylphosphonium chloride.1626 Allyltriphenylphosphonium bromide has been used to produce phosphonium cationic starches.1627... 

Allyltriphenylphosphonium chloride prepared from triphenylphosphine in excess refluxing allyl chloride is far superior to the material synthesized from equimolar amounts of the reagents in boiling benzene because of the tendency of the product to rearrange to propenyltriphenylphosphonium chloride at the higher temperature. Allyltriphenylphosphonium bromide is stable in refluxing benzene. ... 

A Wittig reaction of 1010 with allyltriphenylphosphonium bromide and potassium tert-butoxide produces a 4.3 1 mixture of ZjE dienes, the -diene being the desired isomer. Ring opening of the acetal with diisobutylaluminum hydride and subsequent photoisomerization of... 

Allyltriphenylphosphonium bromide in dry tetrahydrofuran stirred and treated under Ng with Li-diisopropylamide in hexane-tetrahydrofuran, after 0.5 hr. at 20 methyl cw-S-chloropropenoate added dropwise, stirred 2 hrs. at room temp., and treated overnight with excess benzaldehyde all- ra/ij-triene deriv. Y 84%. F. e. s. E. Vedejs and J. P. Bershas, Tetrah. Let. 7975, 1359. 

A suspension of allyltriphenylphosphonium bromide in hexane treated with methyllithium in ether, the resulting soln. stirred 6 hrs. at room temp., ethyl a-isopropylideneacetoacetate dil. with hexane added dropwise at 5-10°, and allowed to stand 1 hr. at room temp. ethyl a-safranate. Y 69%. G. Biidii and H. Wuest, Helv. 54, 1767 (1971) cf. W. G. Dauben et al., Tetrah. Let. 1973, 4425 isocyclics with bridgehead double bonds s. Am. Soc. 95, 5088 (1973) Bredt s rule, review, cf. G. Kobrich, Ang. Ch. 85, 494 (1973). 

Allyltriphenylphosphonium bromide proved to be a useful starting material in the S5mthesis of diphenylphosphine oxide derivatives. The rearrangement of the double bond was followed by the addition of thioalcohol. The final step was the refunctionalization of the P-moiety. Elimination of RSH was a competitive side reaction (Scheme 12). ... 

---