1985
DOI: 10.1271/bbb1961.49.141
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Systematic syntheses and characterization of dodecadien-1-ols with conjugated double bond, lepidopterous sex pheromones.

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Cited by 18 publications
(6 citation statements)
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“…Four geometrical isomers of 4,6-hexadecadien-1-ol and their functional derivatives, acetate and aldehyde, were synthesized by two routes, modifying the previous methods for dodecadienyl compounds with a conjugated diene system, 5) in which one of two double bonds was furnished in a highly stereoselective manner and the other by a Wittig reaction rather nonspeciˆcally. Namely, in the route for Scheme 1 for the (4E,6Z )-and (4E,6E )-isomers, the E conˆgu-ration at the 4-position was derived from stable (E )-2-alkenal 3.…”
Section: Synthesismentioning
confidence: 99%
See 1 more Smart Citation
“…Four geometrical isomers of 4,6-hexadecadien-1-ol and their functional derivatives, acetate and aldehyde, were synthesized by two routes, modifying the previous methods for dodecadienyl compounds with a conjugated diene system, 5) in which one of two double bonds was furnished in a highly stereoselective manner and the other by a Wittig reaction rather nonspeciˆcally. Namely, in the route for Scheme 1 for the (4E,6Z )-and (4E,6E )-isomers, the E conˆgu-ration at the 4-position was derived from stable (E )-2-alkenal 3.…”
Section: Synthesismentioning
confidence: 99%
“…For E4,E6-16:OH and Z4,Z6-16:OH, however, the 13 C assignments could not be established even by 2D NMR experiments because the signals of H 4 and H 7 overlapped each other and those of H 5 and H 6 also overlapped. Therefore, the oleˆnic carbon signals were assigned by utilizing an empirical rule proposed for unbranched conjugated dienes; 5,6) i.e., when an E conˆguration of the , and C d shift upˆeld by ca. 5, 2.5, 2, and 5 ppm, respectively, and the signal of C e shifts downˆeld by ca.…”
Section: C-nmr Analysis Of Hexadecadienyl Compoundsmentioning
confidence: 99%
“…The C10 dienyl alcohols, ( E )‐7,9‐decadien‐1‐ol (E7,9‐10:OH) and ( Z )‐7,9‐decadien‐1‐ol (Z7,9‐10:OH), were previously prepared for a study on the Parasa lepida lepida Cramer pheromone (Islam et al., ). ( E )‐9,11‐dodecadien‐1‐ol (E9,11‐12:OH) and the ( Z )‐isomer (Z9,11‐12:OH) had been synthesized in a previous study (Ando et al., ). Oxidation of the corresponding alcohols with pyridinium chlorochromate in dichloromethane was performed to synthesize ( Z )‐9,11‐dodecadienal (Z9,11‐12:Ald) and ( E )‐9,11‐dodecadienal (E9,11‐12:Ald) (Corey & Suggs, ).…”
Section: Methodsmentioning
confidence: 99%
“…Before field examination, each compound was purified by an opencolumn packed silica gel impregnated with 15% silver nitrate. Three geometrical isomers of E8,E10-12:OH were newly synthesized following previously reported procedures (Ando et al, 1985b) and were purified by the same method for other dienyl pheromones using HPLC with an ODS column (Nishida et al, 2003).…”
Section: Methodsmentioning
confidence: 99%