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Physical Data: mp -119.4 °C; bp 71.3 °C; d 1.398 g cm-3.
Solubility: miscible with organic solvents; sparingly sol H2O.
Form Supplied in: yellow to brown liquid.
Purification: wash with water and with aqueous NaHCO3. Dry (MgSO4 or Na2SO4) and fractionally distill.
Handling, Storage, and Precautions: highly toxic; cancer suspect agent. Protect from light in brown glass.
Similarly, allylation of the lactam by allyl bromide-LDA20 proceeds stereospecifically to give (1).
N-Allylation takes place easily; phthalimide reacts readily with allyl bromide (K2CO3-PEG 400; 90 °C).32 Indoles33a and pyrazoles33b may be allylated on nitrogen using PTC such as Bu4NBr (eq 7).
Salts such as Na phenylsulfinate form allyl esters; Al2O3, ultrasound, and microwaves all influence the yield.34 Correspondingly, sulfur,35,36 selenium,36 or tellurium37 attack is preparatively useful (eq 8).
The allyl system is susceptible to further chemistry, notably epoxidation and other addition processes; the intermediates in such processes may show their own idiosyncratic chemistry39 as in the cyclization of the thioallyl substituent (4) (eq 9), itself obtained by allylation of the thiophenoxide.
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