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539-80-0 - Tropone, 97% - Cycloheptatrienone - L00473 - Alfa Aesar

L00473 Tropone, 97%

CAS Number
539-80-0
Synonyms
Cycloheptatrienone

Size Price ($) Quantity Availability
1g 50.88
5g 176.13
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Tropone, 97%

MDL
MFCD00014331
EINECS
208-725-6

Chemical Properties

Formula
C7H6O
Formula Weight
106.12
Boiling Point
91-92°/4mm
Flash Point
>110°(230°F)
Density
1.094
Refractive Index
1.6150

Literature References

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):

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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).

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For cycloaddition reactions with kinetically stabilized phosphaalkynes, leading to tetracyclic phosphorus-carbon cage compounds, see: J. Org. Chem., 60, 5884 (1995); Synthesis, 87 (1996).

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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).

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Other References

Beilstein
1902335
Harmonized Tariff Code
2914.29
TSCA
No

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