THE ETHYNE-ETHYLIDENE REARRANGEMENT - FORMATION OF 3-ETHYNYLACENAPHTHYLENE AND 1-ETHYNYLACENAPHTHYLENE ON FLASH VACUUM PYROLYSIS OF 1,7-DIETHYNYLNAPHTHALENE
1,7-Diethynylnaphthalene on flash vacuum pyrolysis at 1100-degrees-C/0.05 mm gave 3-ethynylacenaphthylene and 1-ethynylacenaphthylene (80:20). This finding is interpreted in terms of initial formation of 3-ethynylacenaphthylene, ring closure of some of this compound to the hypothetical cyclopent[bc]acenaphthylene and cleavage to give 1-ethynyl- and 3-ethynylacenaphthylene.