Description and references

l-Form is a constituent of rose and geranium oils. d-Form occurs in Ceylon and Java citronella oils. History: J. L. Simonsen, L. N. Owen, The Terpenes vol. I (University Press, Cambridge, 2nd ed, 1947). Prepn of (±)-form: Adams, Garvey, J. Am. Chem. Soc. 48, 477 (1926); Ofner et al., Helv. Chim. Acta 42, 2577 (1959). Prepn of (+)-form: Rien"acker, Ohloff, Angew. Chem. 73, 240 (1961); Naves, Tullen, Helv. Chim. Acta 44, 1867 (1961); Eschinazi, J. Org. Chem. 26, 3072 (1961); Rien"acker, Chimia 27, 97 (1973); C. G. Overberger, J. L. Weise, J. Am. Chem. Soc. 90, 3525 (1968); T. Sato et al., Tetrahedron Lett. 1980, 3377. Prepn of (-)-form: Ohloff, loc. cit.; Rien"acker, loc. cit.; Shono et al., Tetrahedron Lett. 1974, 1295; K. Mori, T. Sugai, Synthesis 1982, 752. Synthesis of (+) or (-)-form from isoprene: Hidai et al., Chem. Commun. 1975, 170. Stereospecific prepn via microbiological (Saccharomyces cerevisiae) reduction: P. Gramatica et al., Experientia 38, 775 (1982). Manuf: Woroch et al.; Bain; Webb, US 2990422; US 3005845; US 3028431 (1961, 1961, 1962, all to Glidden); Eschinasi, US 3052730 (1962 to Givaudan). Abs config of the (+)-form: Freudenberg, Hohmann, Ann. 584, 54 (1953); Freudenberg, Lwowski, ibid. 587, 213 (1954). NMR, HPLC determn of R/S enantiomer ratios: D. Valentine et al., J. Org. Chem. 41, 62 (1976). See also Rhodinol.

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