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Thermal rearrangement of 1-vinylspiro[2.4]hepta-4,6-diene to 4,7-dihydroindene

✍ Scribed by Maitland Jones Jr.; Ronald N. Hochman; James D. Walton


Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
158 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis


THIS BRIEF NOTE is occasioned by recent observations in Germany and the Soviet Union. SchGnleber3 has remarked the thermal conversion of 1-vinylspiro[2.4]hepta-4,6-diene (l-1 to indane at 350Β°. In related work, Mironov, et al. 4 --reported the rearrangement of spiro[4.4]nona-1,3-diene

to indane at 300-400s. In the latter case, several tetrahydroindene intermediates were isolated. We describe here the isolation of a compound


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Organocuprates react with spiro [2,4]heptadiene 4-nitrile to furnish ring-opened cyclopentadiene adducts which can be chemoselectively monohydrogenated to the corresponding unsaturated cyclopentene nitriles. The use of optically active spiro [2,4]heptadiene ,allows for the asymmetric synthesis of ch