6-CYCLOPROPYL- AND 6-(1-METHYLCYCLOPROPYL)-1,4-BENZODIOXANES: SYNTHESIS AND NITRATION. REARRANGEMENT OF NITRO SUBSTITUTED 6-CYCLOPROPYL-1,4-BENZODIOXANES USING CONCENTRATED SULFURIC ACID

Article abstract of DOI:10.1007/BF01169933

6-Cyclopropyl- and 6-(1-methylcyclopropyl)-1,4-benzodioxanes have been synthesized as the first cyclopropyl-1,4-benzodioxanes.It was shown that nitration of these compounds occurs with retention of the three carbon ring.In contrast to simple ethers of cyclopropylphenols, nitration leads only to 7-nitro-6-cyclopropyl- and 7-nitro-6-(1-methylcyclopropyl)-1,4-benzodioxanes, respectively.Nitration of 7-nitro-6-cyclopropyl-1,4-benzodioxane occurs regioselectively to give exclusively the 7,8-dinitro product.The structure of the nitration products was confirmed by their rearrangement to the corresponding nitrosopropionyl-1,4-benzodioxanes.