108661-11-6Relevant articles and documents
Silver Ion-Assisted Solvolysis of 8,11-Dibromolongibornane: Generation of Novel Skeletally Rearranged Olefinic Carbinols
Reddy, R. Thimma,Nayak, U. R.
, p. 585 - 588 (2007/10/02)
The disecondary bromide, 8,11-dibromolongibornane (3) on exposure to silver perchlorate in aqueous acetone gives predominantly a mixture of three olefinic carbinols, of which a unique ring-expanded alcohol (7) constitutes 65percent; the assigned structure has been confirmed by an X-ray anaylsis of its p-bromobenzoate.Of the other two minor alcohols (separable only in the form of their ketones), one has been characterized as 10-ketolongifolene (15); the other keto-olefin which is highly hindered and resistant to Wolff-Kishner reduction has been assigned one of two possible structures 12/13 based on spectral data.The minor hydrocarbon fraction (6percent) has been shown to consist of two compounds of which only one has beencharacterized as dehydrolongifolene (22).