CA1048532A - Cis-olefines - Google Patents

Cis-olefines

Info

Publication number: CA1048532A
Authority: CA; Canada
Prior art keywords: cis; formula; olefins; acid triamide; alkyl
Prior art date: 1973-11-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA74213170A

Other languages

English (en)

Other versions

CA213170S (en

Inventor

Otto Vostrowsky

Hans J. Bestmann

Werner T. Stransky

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-11-07

Filing date

1974-11-06

Publication date

1979-02-13

1974-11-06 Application filed by Hoechst AG filed Critical Hoechst AG

1979-02-13 Application granted granted Critical

1979-02-13 Publication of CA1048532A publication Critical patent/CA1048532A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 8
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
150000001340 alkali metals Chemical class 0.000 claims abstract description 8
150000004714 phosphonium salts Chemical class 0.000 claims abstract description 8
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 7
239000011541 reaction mixture Substances 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
150000001336 alkenes Chemical class 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
229910052700 potassium Inorganic materials 0.000 claims description 9
239000011591 potassium Substances 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
125000006732 (C1-C15) alkyl group Chemical group 0.000 claims 1
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 5
238000009835 boiling Methods 0.000 description 18
150000001875 compounds Chemical class 0.000 description 13
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003016 pheromone Substances 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000000877 Sex Attractant Substances 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000306 component Substances 0.000 description 3
-1 formyloxy Chemical group 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XDBKLFODBADBED-YPKPFQOOSA-N (z)-2-methyloctadec-7-ene Chemical compound CCCCCCCCCC\C=C/CCCCC(C)C XDBKLFODBADBED-YPKPFQOOSA-N 0.000 description 2
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
LIOHXTBHAXATAT-UHFFFAOYSA-N 9-oxononyl acetate Chemical compound CC(=O)OCCCCCCCCC=O LIOHXTBHAXATAT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
241000255777 Lepidoptera Species 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
PAHGTQWKVSZQDW-UHFFFAOYSA-N 1-oxononan-2-yl acetate Chemical compound CCCCCCCC(C=O)OC(C)=O PAHGTQWKVSZQDW-UHFFFAOYSA-N 0.000 description 1
ACMPVOBGYDUYKN-UHFFFAOYSA-N 11-oxoundecyl acetate Chemical compound CC(=O)OCCCCCCCCCCC=O ACMPVOBGYDUYKN-UHFFFAOYSA-N 0.000 description 1
OQXUXRZOOWDNIX-UHFFFAOYSA-N 9-oxononyl formate Chemical compound O=CCCCCCCCCOC=O OQXUXRZOOWDNIX-UHFFFAOYSA-N 0.000 description 1
241000175828 Adoxophyes orana Species 0.000 description 1
241001574379 Ancylis Species 0.000 description 1
241001525898 Argyrotaenia velutinana Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000726763 Cadra Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241001124562 Choristoneura rosaceana Species 0.000 description 1
241000255967 Helicoverpa zea Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
241000721703 Lymantria dispar Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001147398 Ostrinia nubilalis Species 0.000 description 1
241000497111 Paralobesia viteana Species 0.000 description 1
241000595626 Plodia Species 0.000 description 1
241000500437 Plutella xylostella Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241001198112 Rhyacionia buoliana Species 0.000 description 1
241000074773 Rhyacionia duplana Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000256248 Spodoptera Species 0.000 description 1
241000256247 Spodoptera exigua Species 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000006701 autoxidation reaction Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
FKLSONDBCYHMOQ-ARJAWSKDSA-N cis-9-dodecenoic acid Chemical compound CC\C=C/CCCCCCCC(O)=O FKLSONDBCYHMOQ-ARJAWSKDSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940079826 hydrogen sulfite Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
VAUKWMSXUKODHR-UHFFFAOYSA-M pentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC)C1=CC=CC=C1 VAUKWMSXUKODHR-UHFFFAOYSA-M 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000000047 product Substances 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA74213170A 1973-11-07 1974-11-06 Cis-olefines Expired CA1048532A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732355534 DE2355534A1 (de)	1973-11-07	1973-11-07	Verfahren zur herstellung von cisolefinen

Publications (1)

Publication Number	Publication Date
CA1048532A true CA1048532A (fr)	1979-02-13

Family

ID=5897374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA74213170A Expired CA1048532A (fr)	1973-11-07	1974-11-06	Cis-olefines

Country Status (10)

Country	Link
JP (1)	JPS5077303A (fr)
BE (1)	BE821951A (fr)
CA (1)	CA1048532A (fr)
CH (1)	CH605486A5 (fr)
DE (1)	DE2355534A1 (fr)
FR (1)	FR2249860B1 (fr)
GB (1)	GB1457337A (fr)
IL (1)	IL45977A (fr)
IT (1)	IT1025448B (fr)
NL (1)	NL7414299A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU176515B (en) *	1978-04-21	1981-03-28	Egyt Gyogyszervegyeszeti Gyar	Composition for enticing male agrotis of cabbage
DE2834872A1 (de) *	1978-08-09	1980-02-21	Hoechst Ag	Insektenlockstoff
US6838576B1 (en)	2003-10-23	2005-01-04	3M Innovative Properties Company	Process for preparing functional group-containing olefinic compounds
JP2008280289A (ja) *	2007-05-10	2008-11-20	Jfe Chemical Corp	１−メチレンインダン骨格を有する不飽和化合物の製造方法

1973
- 1973-11-07 DE DE19732355534 patent/DE2355534A1/de active Pending
1974
- 1974-11-01 IL IL45977A patent/IL45977A/en unknown
- 1974-11-01 NL NL7414299A patent/NL7414299A/xx unknown
- 1974-11-04 CH CH1475574A patent/CH605486A5/xx not_active IP Right Cessation
- 1974-11-05 GB GB4778774A patent/GB1457337A/en not_active Expired
- 1974-11-05 IT IT29133/74A patent/IT1025448B/it active
- 1974-11-06 CA CA74213170A patent/CA1048532A/fr not_active Expired
- 1974-11-06 JP JP49127254A patent/JPS5077303A/ja active Pending
- 1974-11-07 FR FR7436923A patent/FR2249860B1/fr not_active Expired
- 1974-11-07 BE BE150296A patent/BE821951A/fr unknown

Also Published As

Publication number	Publication date
IL45977A (en)	1977-12-30
GB1457337A (en)	1976-12-01
JPS5077303A (fr)	1975-06-24
NL7414299A (nl)	1975-05-12
BE821951A (fr)	1975-05-07
IL45977A0 (en)	1975-02-10
CH605486A5 (fr)	1978-09-29
IT1025448B (it)	1978-08-10
FR2249860A1 (fr)	1975-05-30
FR2249860B1 (fr)	1978-02-24
DE2355534A1 (de)	1975-09-11

Publication	Publication Date	Title
Millar et al.	1983	Synthesis of two macrolide aggregation pheromones from the flat grain beetle, Cryptolestes pusillus (Schönherr)
US4540826A (en)	1985-09-10	Process for preparing olefinic aldehydes
Bessière et al.	1977	Solvolytic Ring‐opening of Alkoxychlorofluorocyclopropanes: A Ready Access to Fluorinated α, β‐Unsaturated Aldehydes and Ketones
Mukaiyama et al.	1981	A convenient synthesis of α-hydroxyallenes by the reaction of propargyl iodides with aldehydes in the presence of stannous halide
CA1048532A (fr)	1979-02-13	Cis-olefines
Büchi et al.	1979	Macrocycles by Olefination of Dialdehydes with 1, 3‐Bis (dimethylphosphono)‐2‐propanone
US4057593A (en)	1977-11-08	Process for preparing cis-olefins
US4118406A (en)	1978-10-03	Process for preparing cis-olefins
US5208381A (en)	1993-05-04	Method for the manufacture of carotinoids and novel intermediates
Mori	1974	A New Synthesis of 2-Methyl-6-methyleneocta-2, 7-dien-4-ol, A Component of the Pheromone of California Five-spined Ips
US5061819A (en)	1991-10-29	Methods for synthesizing phosphonate reagents and retinoids
Uchida et al.	1981	Syntheses of 2, 6-dimethyl-1, 5-heptadien-3-ol acetate, the pheromone of the Comstock mealybug Pseudococcus comstocki Kuwana, and its analogs
Shani	1979	An efficient synthesis of muscalure from jojoba oil or oleyl alcohol
Anderson et al.	1979	Synthesis of 7-methyl-3-methylene-7-octen 1-yl propanoate and (z)-3, 7-dimethyl-2, 7-octadien-1-yl propanoate, components of the sex pheromone of the san jose scale
Ebata et al.	1979	A Convenient Synthesis of a Mixture of (Z, Z)-3, 13-Octadecadienyl Acetate and Its (E, Z)-Isomer, the Attractant for the Cherrytree Borer
Boland et al.	1982	Synthesis of (±)‐Desmarestene and (±)‐Viridiene, the Two Sperm Releasing and Attracting Pheromones from the Brown Algae Desmarestia aculeata and Desmarestia viridis
Kumar et al.	2018	Synthesis of sex pheromones of the citrus leafminer (CLM)(Phyllocnistis citrella)
Inoue et al.	1990	Cis selective wittig olefination of. ALPHA.-alkoxy ketones and its application to the stereoselective synthesis of plaunotol.
Fujisawa et al.	1982	A novel synthesis of royal jelly acids and queen substance by the five carbon homologation using β-vinyl-β-propiolactone
Takigawa et al.	1975	Synthesis and biological activity of some juvenile hormone analogs lacking the alkyl substituents at C-7 or both at C-3 and at C-7
Cochrane et al.	1972	Syntheses of the insect juvenile hormone
US3856866A (en)	1974-12-24	Synthesis of codling moth attactant
GB2210040A (en)	1989-06-01	Preparation of 3-(4'-bromobiphenyl-4-YL) tetralin-1-one
US4571438A (en)	1986-02-18	Process for preparing olefinic aldehydes and chemical intermediates
Taguri et al.	2010	Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth