Propenyl

In organic chemistry, 1-propenyl (or simply propenyl) has the formula CH=CHCH₃ and 2-propenyl (isopropenyl) has the formula CH₂=C-CH₃. These groups are found in many compounds. Propenyl compounds are isomeric with allyl compounds, which have the formula CH₂-CH=CH₂.

The three common precursors to lignin are derivatives of propenylbenzene: paracoumaryl alcohol (1), coniferyl alcohol (2) and sinapyl alcohol (3).

Chemicals with 1-propenyl groups

• 2-chloropropylene
• propenylbenzene (β-methylstyrene).^[1]

Many phenylpropanoids and their derivatives feature derivatives of propenylbenzene:

• Anethole
• Asarone
• Carpacin
• Coniferyl alcohol
• Isoeugenol
• Isosafrole
• Methyl isoeugenol
• Pseudoisoeugenol

Chemicals with 2-propenyl groups

p-Isopropenylphenol features a 2-propenyl derivative of phenol.

Isopropenyl acetate is a 2-propenyl ester, synthesizable from ketene.

Several terpenes feature 2-propenyl substituents:

• carvone
• limonene

See also

• Propene
• Functional group

References

1. Linstrumelle, Gerard; Krieger, Jeanne K.; Whitesides, George M. (1976). "Preparation of Alkenes by Reaction of Lithium Dipropenylcuprates with Alkyl Halides: (E)-2-Undecene" (PDF). Org. Synth. 55: 103. doi:10.15227/orgsyn.055.0103.