Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1′-cyclopropane] derivatives

Reactions of benzyne with ester derivatives of spiro[2.4]hepta-4,6-dien-1-ylmethanol were performed. By rearrangement reaction of cyclopropyl methanol units of ((1s*,1'R*,2R*,4'S*)-1',4'-dihydrospiro [cyclopropane-1,9'-[1,4]methanonaphthalen]-2-yl) methyl 3,5-dinitrobenzoate (13) and its isomer (14), corresponding allyl chlorides were obtained. Two rearrangement products were obtained from bromination of compound 13 with an equivalent amount of Br-2. A naphthalene derivative including allyl and CHO moiety was formed for reactions from compounds with epoxide of 13 and 14 with NaN3 by sequential rearrangements. Formations of products are discussed. (C) 2018 Elsevier Ltd. All rights reserved.