Process for opening cyclopropane rings

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549 51, 549 60, 549 62, 549 66, 549 78, 549505, 549506, 549497, 549504, 549479, 568655, 568656, 570128, 570182, 570185, 585476, 585506, 546346, 546348, 546288, 546280, 546275, 546283, 546284, 548182, 548183, 548202, 548213, 548206, C07D33308, C07D30736

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051264617

ABSTRACT:
Process for ring opening compounds of the formula ##STR1## in which R.sup.1 is heteroaryl or aryl, R.sup.2 is a leaving group, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently selected from hydrogen, alkyl, aralkyl, aryl, heteroaryl and alkenyl, provided that at least one of the groups R.sup.3 to R.sup.6 is other than hydrogen, by breaking the bond joining the carbon atom attached to R.sup.3 and the carbon atom attached to R.sup.6 in organic solution using silica, giving useful diene or allyl derivatives, certain of which are novel.

REFERENCES:
Reese, C. B., "Stereochemistry of Solvolysis of Halogenocarbene Adducts of Cyclic Olefins", J. Chem. Soc. Chem. Comm., 1970, pp. 1365-1366.
Meisels, G. G., et al., "Ionization and Dissociation of C.sub.4 H.sub.8 Isomers", J. Amer. Chem. Soc., vol. 92, 1970, pp. 254-258.
Alonso, Miguel E., et al., "Synthesis of Alpha-Carboxy-Gamma-Butyrolactones on Silica Surfaces", J. Heterocyclic Chem., vol. 19, Mar.-Apr. 1982, pp. 369-371.
Baird, M. S. et al., "Silver-Induced Ring-Opening of Some Tri-Tetrahalogenocyclopropanes", J. Chem. Research, 1988, pp. 292-293.
A. Padwa, J. Chem. Soc. Perkin I, "Photorearrangement Studies of 3-Heteroaryl-Substituted Cyclopropanes", pp. 2671-2676 (1984).

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