Identification and Synthesis of the Four Compounds Comprising the Boll Weevil Sex Attractant

James Homer Tumlinson, III; J. P. Minyard; R. C. Gueldner; D. D. Hardee; A. C. Thompson; P. A. Hedin

doi:10.1021/jo00817a012

Identification and Synthesis of the Four Compounds Comprising the Boll Weevil Sex Attractant

James Homer Tumlinson, III, J. P. Minyard, R. C. Gueldner, D. D. Hardee, A. C. Thompson, P. A. Hedin

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116 Scopus citations

Abstract

Four terpenoid compounds, (+)-cis-2-isopropenyl-1-methylcyclobutaneethanol, (1), Z-3,3-dimethyl-Δ¹, -cyclohexaneethanol (2), Z-3,3-dimethyl-Δ_1,∝-cyclohexaneacetaldehyde (3), and E-3,3-dimethyl-Δ_1,∝-cyclo-hexaneacetaldehyde (4), weee identified as the components of the male sex pheromone of the boll weevil. The synthesis and structural assignments of the four compounds are also reported.

Original language	English (US)
Pages (from-to)	2616-2621
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	36
Issue number	18
DOIs	https://doi.org/10.1021/jo00817a012
State	Published - Sep 1 1971

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All Science Journal Classification (ASJC) codes

Organic Chemistry

Cite this

Tumlinson, III, J. H., Minyard, J. P., Gueldner, R. C., Hardee, D. D., Thompson, A. C., & Hedin, P. A. (1971). Identification and Synthesis of the Four Compounds Comprising the Boll Weevil Sex Attractant. Journal of Organic Chemistry, 36(18), 2616-2621. https://doi.org/10.1021/jo00817a012

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abstract = "Four terpenoid compounds, (+)-cis-2-isopropenyl-1-methylcyclobutaneethanol, (1), Z-3,3-dimethyl-Δ1, -cyclohexaneethanol (2), Z-3,3-dimethyl-Δ1,∝-cyclohexaneacetaldehyde (3), and E-3,3-dimethyl-Δ1,∝-cyclo-hexaneacetaldehyde (4), weee identified as the components of the male sex pheromone of the boll weevil. The synthesis and structural assignments of the four compounds are also reported.",

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AU - Tumlinson, III, James Homer

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AU - Gueldner, R. C.

AU - Hardee, D. D.

AU - Thompson, A. C.

AU - Hedin, P. A.

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AB - Four terpenoid compounds, (+)-cis-2-isopropenyl-1-methylcyclobutaneethanol, (1), Z-3,3-dimethyl-Δ1, -cyclohexaneethanol (2), Z-3,3-dimethyl-Δ1,∝-cyclohexaneacetaldehyde (3), and E-3,3-dimethyl-Δ1,∝-cyclo-hexaneacetaldehyde (4), weee identified as the components of the male sex pheromone of the boll weevil. The synthesis and structural assignments of the four compounds are also reported.

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10.1021/jo00817a012