1504-04-7Relevant articles and documents
Reactions of 6,8-Dioxabicyclo(3.2.1)oct-3-ene and 6,8-Dioxabicyclo(3.2.1)oct-2-ene with Lithium Aluminium Hydride
Majumdar, K. C.,Ranganayakulu, K.,Brown, R. K.
, p. 303 - 306 (2007/10/02)
Reduction of 6,8-dioxabicyclo(3.2.1)oct-3-ene (6) with lithium aluminium hydride in refluxing 1,2-dimethoxyethane gives 2-hydroxymethyl-3,4-dihydro-2H-pyran (7) in an excellent yield.However, under identical conditions 6,8-dioxabicyclo(3.2.1)oct-2-ene (8) gives a mixture of 4-hexen-1-ol (9), 5-hexen-1-ol (10) and 2-hexene-1,6-diol (11).When 6 is refluxed with LAH in di-n-propyl ether, 7 is obtained in addition to 2-hydroxymethyl-2,3-dihydro-6H-pyran (33).However, compound 8 remains unaffected by LAH under similar conditions.