ChemInform Abstract: REDUCTION OF P‐CYMENE BY THE LITHIUM‐ETHYLENEDIAMINE SYSTEM

Bazyl'chik, V. V.; Fedorov, P. I.

doi:10.1002/chin.197735373

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1984

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“…The styrene ( 259) is reduced to o-cymene (260) by Ca(NH3), in hexane;206 (260) can be further reduced by the same reagent to o-mentha-l,4-diene (261). 207 The o-mentha-l,3-dienolide (262) is found in the urine of the koala bear, Phascolarctos cinereus, and has now been synthesized by the Diels-Alder reaction of l-acetoxybuta-l,3-diene with the lactone (263) to give (264), which yields (262) on treatment with LiL208 Unlike most ap-unsaturated lactones, ( 263) is a good dienophile. The ortho-menthenes ( 265) and ( 266) have been prepared in the same way as were ( 219) and ( 220) in the para-series.177 ( + )-(3R)-Sylvestrene (267) reacts with singlet oxygen to give ( 268)- (270).…”

Section: Menthanesmentioning

confidence: 99%