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Reacts as a diene in the Diels-Alder reaction with electron-rich alkenes (inverse electron-demand); see, e.g.: Org. Synth. Coll., 9, 396 (1998):/n
Alternatively, reaction can occur with electron-deficient alkenes, as exemplified by phenyl vinyl sulfoxide. In this case, cyclic elimination leads directly to bicyclo[3.2.2]nona-3,6,8-trien-2-one in low yield: J. Org. Chem., 48, 3591 (1983). For a review of cycloadducts of tropone and its analogs with sulfenes and ketenes, see: Heterocycles, 18, 343 (1982)./n
For cycloaddition reactions with kinetically stabilized phosphaalkynes, leading to tetracyclic phosphorus-carbon cage compounds, see: J. Org. Chem., 60, 5884 (1995); Synthesis, 87 (1996)./n
Reacts with Grignard reagents at the 2-position (1,6-addition) as in the first step of a synthesis of the hydroazulene skeleton: Tetrahedron Lett., 23, 1863 (1982). Addition of various Li enolates again leads to 2-substituted 2,6-dihydrotropones in good yield: J. Org. Chem., 53, 4596 (1988)./n
Precautionary Statements: P260-P201-P280-P304+P340-P405-P501a
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