Abstract:The reduction of 2-alkoxymethylthiiranes with lithium aluminum hydride has been found to result in the formation of 1alkoxy-2-mercaptopropanes, the isomers expected from normal ring fission. The reaction of triethyl phosphite with the 1alkoxy-2-mercaptopropanes was found to result in the formation of the corresponding alkyl propyl ethers and triethyl thionophosphate. The reaction of 2-alkoxymethylthiiranes with the secondary amines, piperidine, morpholine, and diethylamine w-as also investigated. The yield of … Show more
“…The yields of mercaptans amounted to 72% for propene sulfide (22), 73% for 1-hexene sulfide (22), 20% for 1-octene sulfide (153), and 75-85% for a number of 3-alkoxypropene sulfides (110). The reduction of cyclohexene sulfide (22,159) and carbohydrate thiiranes (36) with L1AIH4 was also reported.…”
“…The yields of mercaptans amounted to 72% for propene sulfide (22), 73% for 1-hexene sulfide (22), 20% for 1-octene sulfide (153), and 75-85% for a number of 3-alkoxypropene sulfides (110). The reduction of cyclohexene sulfide (22,159) and carbohydrate thiiranes (36) with L1AIH4 was also reported.…”
“…Thus, photolysis of aromatic iodides has led to syntheses of biphenyls, phenanthrenes, and organophosphorus and organoboron compounds, all in acceptable yields. 3 Aromatic iodo compounds are now readily accessible from a wide variety of aromatic hydrocarbons through initial thallation with thallic trifluoroacetate followed by treatment with aqueous potassium iodide,4 and we (1) We gratefully acknowledge partial financial support of this work by the Smith Kline and French Laboratories, Philadelphia, Pa.…”
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