Studies on Lewis acid-mediated intramolecular cyclization reactions of allene-ene systems.
The Lewis acid-mediated reactions of allene-ene compounds, derived from 3-methylcitronellal or dimethyl malonate, were carried out using various Lewis acids such as ethylaluminum dichloride, diethylaluminum chloride, titanium chloride, zinc chloride etherate, or boron trifluoride etherate, affording unexpectedly intramolecular [2+2]cycloaddition products under some particular reaction conditions without any formation of intramolecular ene reaction products.
Hiroi
K
K
Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, Sendai, Miyagi, Japan.
Watanabe
T
T
Tsukui
A
A
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry*; D003500:Cyclization; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000737:chemistry
D000447:Aldehydes; D000466:Alkadienes; D007202:Indicators and Reagents; D008314:Malonates; D013729:Terpenes; C005230:methyl malonate