Papers by Arne Van Der Gen
The Journal of Organic Chemistry, 1990
Tetrahedron, 1998
Acid promoted ring opening of la,4a,4act,9aa-tetrahydro-21B-31B-elx3xy-1,4-methanoanthracene-9,10... more Acid promoted ring opening of la,4a,4act,9aa-tetrahydro-21B-31B-elx3xy-1,4-methanoanthracene-9,10-dione and the corresponding 2-methyl de,'ivative (i.e., 3a and 3b, respectively) afforded 4a and 4b in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 4b along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of la,4a-dihydro-4act,9act-epoxy-l,4-methanoanthracene-9,10-dione (12) resulted in extensive skeltal rearrangement of the substrate, thereby affording 14 in low yield.
Accounts of Chemical Research, 1991
We should note here that a similar and perhaps more realistic transition-state model can be const... more We should note here that a similar and perhaps more realistic transition-state model can be constructed based on the folded envelope-like conformations of methylenecyclopentane. However, we find the cyclohexane model to be more useful, albeit less preciee, simply because the conformational preferences are better understood in the cyclohexane system than in methylenecyclopentanes,
Bulletin of the Chemical Society of Japan, 1984
The Journal of Organic Chemistry, 1987
Isolation of the Hydrogenated Products of 11. The resulting mixture was chromatographed on silica... more Isolation of the Hydrogenated Products of 11. The resulting mixture was chromatographed on silica gel with hexane 1.518), 15 (n=D 1.480), 13 (nED 1.520), and 3-phenylcyclohexanone (2,4-dinitrophenylhydrazone (mp 178-180 "C, dec; lit.27 mp 182-186 "C) in this order. Acknowledgment. Toshikatsu Funahara and Tooru Kawata provided helpful technical assistance as graduation theses for which we thank them. M.M. greatly appreciates the helpful advice of Professor
Recueil des Travaux …, 1984
... Chem. 665, 9 1 (1963). R. Burgada and J. Roussel, Bull. SOC. ... 273 1 (1 976); M. Mikolajczy... more ... Chem. 665, 9 1 (1963). R. Burgada and J. Roussel, Bull. SOC. ... 273 1 (1 976); M. Mikolajczyk, S. Grzejszczak, A . Zatorski, B. Mlotkowska, H. Gross and B. Costisella, Tetrahedron 34, 3081 (1978); C. G. Kruse, NLJ M. Broekhof, A. Wijsman and A. van der Gen, Tetrahedron Lett. ...
Tetrahedron, 1996
... References. 1. TAM Van Schaik, AV Henzen and A. Van der Gen. Tetrahedron Lett. 24 (1983), pp.... more ... References. 1. TAM Van Schaik, AV Henzen and A. Van der Gen. Tetrahedron Lett. 24 (1983), pp. 13031306. ... 311 (1969), pp. 577585. Full Text via CrossRef. 6. NLJM Broekhof, P. Van Elburg and A. Van der Gen. Recl. Trav. Chim. Pays-Bas 103 (1984), pp. 312316. ...
… des Pays-Bas, 1985
... K. C. NicoZaou, R. Zipkin and D. Tanner, J.Chem. Soc. , Chem. Comm. 349 (1984). The optical r... more ... K. C. NicoZaou, R. Zipkin and D. Tanner, J.Chem. Soc. , Chem. Comm. 349 (1984). The optical rotation of the natural product is unknown (Dr DGIKingston, personal communica-tion). PP de Wit, TAM van Schaik and A. vap der Gen, Recl.Trav.Chim. Pays-Bas 103, 369 (1984). ...
Tetrahedron Letters, 1980
... 11 1 CH3 0 Li 11 1 ZCH3 CH3 R1 1. Ph 2PCHN Ph2PCN R1 N Ph 1 Ph KOtBu Ph R2 2. NH4CI RIC OH R2... more ... 11 1 CH3 0 Li 11 1 ZCH3 CH3 R1 1. Ph 2PCHN Ph2PCN R1 N Ph 1 Ph KOtBu Ph R2 2. NH4CI RIC OH R2 HA 12 R 4 E + Z 5 In order to complete the HornerWittig reaction, the adducts 4 were ... 2. NLJM Broekhof, FL Jonkers and A. van der Gen, Tetrahedron Letters 1979, 2433. ...
Tetrahedron Letters, 1979
... ENAMINE SYNTHESIS BY THE HORNERWITTIG REACTION NLJ,M. Broekhof, FL Jonkers and A, van der Gen... more ... ENAMINE SYNTHESIS BY THE HORNERWITTIG REACTION NLJ,M. Broekhof, FL Jonkers and A, van der Gen 31 Gorlaeus Laboratories, Department of Organic Chemistry, University of Leiden ... 0 Li 0 R 1 1. Ph2P CH Ph2t'CHNo R 1 2 2. NH C1 HOR1 2 HR 4 R R2 2 3 Generally ...
Recueil des Travaux …, 1984
A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on... more A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on the Horner-Wittig reaction. Coupling of the anion of the glyceryl substituted phosphine oxide 7 with unsaturated aldehydes 9a-c provided, after treatment ...
Recueil des Travaux …, 1984
A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on... more A synthesis of racemic fecapentaene-12 and other glyceryl enol ethers has been developed based on the Horner-Wittig reaction. Coupling of the anion of the glyceryl substituted phosphine oxide 7 with unsaturated aldehydes 9a-c provided, after treatment ...
Biochemical Pharmacology, 1980
Two mechanisms for the toxic actions of 1,2-dibromoethane have been postulated.
… des Pays-Bas, 1986
... Pays-Bas 105,449-455 (1986) The use of sulfenyl halides in the synthesis of mercapturic acids... more ... Pays-Bas 105,449-455 (1986) The use of sulfenyl halides in the synthesis of mercapturic acids and their esters# Wim Buijs', Mohammed IA Eid', Willem Onkenhout', Nico P. E. Vermeulen' and Arne van der Gen' ... 26, 275 (1979). Dr. M. Teunissen, personal communication. 2 1 ...
Journal of Agricultural …, 1971
... Details about Italian onion oils are described by Giusti (1968). Dutch onions (white type, fa... more ... Details about Italian onion oils are described by Giusti (1968). Dutch onions (white type, familyVictoria) and Egyptian onions (yellow type), harvested in 1969, were investigated during spring 1970. For the headspace analysis onions were cut in two. ...
Accounts of Chemical Research, 1968
Formolysis of the dienic sulfonate esters 17 and 20 gives bicyclic products which belong exclusiv... more Formolysis of the dienic sulfonate esters 17 and 20 gives bicyclic products which belong exclusively to the trans-and cis-decalin series, respectively. Although the yield of bicyclization is low, the stereochemical course of the reaction is dictated by the configuration of the substrates according to the Stork-Eschenmoser hypothesis. Acetolysis of the trienic sulfonate ester 23 (R = S02CaH4N02) affords tricyclic material 24 in very poor yield, but the process is highly stereoselective. Stannic chloride catalyzed cyclization of the dienic acetals 31 and 32 proceeds in high yield and with high stereoselectivity to give trans-and cis-decalin derivatives. The all-trans trienic acetal 46 (R = H) similarly gives rise exclusively to trans,anti,trans
Directly generated potassium enolates of aldehydes reaot with diphenyldisulfide to give the a-sul... more Directly generated potassium enolates of aldehydes reaot with diphenyldisulfide to give the a-sulfenylated aldehydes. Reaction with iodine likewise provides the a-iodo aldehydee. In a previous paper the direct alkylation of aldehydes via their potassium enolates was
Biotechnology and …, 2001
A process model for the enzymatic synthesis of (R)-cyanohydrins in an aqueous-organic biphasic-st... more A process model for the enzymatic synthesis of (R)-cyanohydrins in an aqueous-organic biphasic-stirred tank reactor was developed. The conversion of benzal-dehyde into (R)-mandelonitrile, catalyzed by Prunus amygdalus hydroxynitrile lyase at 5°C and pH ...
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Papers by Arne Van Der Gen