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Toyota, S.; Iwanaga, T., Science of Synthesis, (2010) 45, 764.
3,4-Dihydronaphthalen-1(2H)-one (1-tetralone) (78, R1 = H) is a key compound of the conventional synthetic methods for the synthesis of substituted naphthalenes. This compound is usually prepared by intramolecular Friedel–Crafts acylation of 4-phenylbutanoic acid (77, R1 = H) (Scheme 24).[65,66] In the classical synthesis, 4-phenylbutanoic acid (77, R1 = H) is directly cyclized by treatment with phosphorus pentoxide[67] or sulfuric acid,[68] or its acid chloride is cyclized in the presence of aluminum trichloride[69] or tin(IV) chloride.[70] 3,4-Dihydronaphthalen-1(2H)-one is also synthesized by aluminum trichloride catalyzed cyclization of benzene with γ-butyrolactone (79, R1 = H) in a one-pot reaction (Scheme 24).[70] The yields of these cyclization reactions are generally high. The above reactions require either a stoichiometric or excess amount of strong or Lewis acids. To reduce the waste, environmentally friendly reactions have been developed, for example using mild Lewis acids or polymer-supported strong acids.[71–73] Thus prepared, tetralones can be converted into various naphthalenes by various methods (see Section 45.19.1.1.3.2).
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88 | [88] |
88 | M | 8. MMMe8 8. MeMe8, MM8, eeee |
88 | [88] |
88 | M | M8M8, eeee | 88 | [88] |
88 | Me | M8MM8, eeee | 88 | [88] |
88 | M | eeeeeee, MeMe8, eeee | 88 | [88] |
88 | Me | eeeeeee, MeMe8, eeee | 88 | [88] |
References
[65] | Meeeeeeeee, M. M.; Meeee, M. M. M., Mee. Meeee., Meee. Mee. MM, (8888), 88. |
[66] | Meeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[67] | Meeeee, M. M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 888. |
[68] | Meeeeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
[69] | Meeeee, M. M.; Meeeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[70] | Meeee, M. M.; Meeee, M. M., Mee. Meeee., Meee. Mee. MM, (8888), 888. |
[71] | Mee, M.-M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[72] | Meeeee, M.; Meeeeeeee, M.; Meeeeee, M. M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[73] | Meeeeeeee, M.; Meeeee, M., Meee. Meee., (8888), 8888. |
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- 8.Meeeee-Meee, (8888) 8/8e8, 888.
- 8.Meeeee-Meee, (8888) M 8-8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
- 8.Meeeee-Meee, (8888) M 8e, 888.