Furylmethyl alcohols

The change in the alcohol moiety to allethrone led to the development of the first synthetic pyrethroid, allethrin. It also led to improved chemical stability of the natural pyrethrins and to reduced cost, because the original pyrethrins had been sourced from natural products (LaForge and Soloway 1947). The stability of alle-thrin made it superior to the natural pyrethrins in both kill and knock-down effects against mosquitoes. Allethrin s successful discovery was followed by the development of other successful pyrethroids, to wit, tetramethrin (Kato et al. 1965) (1965, patent appl date) from tetrahydrophtalimide, resmethrin (Elliott et al. 1967) (1967, patent appl date) from 5-benzyl-3-furylmethyl alcohol and phenothrin (Fujimoto et al. 1973) (1968, patent appl date) by changing a-benzylfuran to phenoxyphenyl. 

Furan-2-carbaldehyde 8 is commonly referred to as furfural. It is produced on a large scale by the action of acids on sugars and is a commercially important raw material used in furfural-phenol resins and as a synthetic intermediate . The 2-furylmethyl radical is called furfuryl and, for example, the alcohol 9 is commonly known as furfuryl alcohol. The furan derivative 10 (ranitidine) was one of the first H2-antagonists for the treatment of gastric ulcers and a major contribution to modern medicine. 

The selenoxide can become the more stable form if the double bond is incorporated in an aromatic 7t-eleclron system, for example in the case of furylmethyl or phenanthrylmethyl selenoxides4, or if angle strain diminishes the stability of the selenate, for example in the case of 1-vinylcyclopropyl phenyl selenoxides6. However, treatment of these selenoxides with a secondary amine results in fast conversion to the allylic alcohols, indicating that the selenate, while not directly observed, is in equilibrium with the selenoxide. 

Furyl methanal. See Furfural 2-Furylmethanethiol. See Furfuryl mercaptan (2-Furyl) methanol. See Furfuryl alcohol 2-Furylmethyl butanoate. See Furfuryl butyrate 2-Furyl methyl ketone. See 2-Acetylfuran... 

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