Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents

G.J.M. Vos; P.H. Benders; R.J.M. Egberink; D.N. Reinhoudt; S. Harkema; G.J. van Hummel; A. J.A. van der Weerdt; A.J.A. van der Weerdt

doi:10.1002/recl.19861051011

Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents

G.J.M. Vos^*, P.H. Benders, R.J.M. Egberink, D.N. Reinhoudt, S. Harkema, G.J. van Hummel, A. J.A. van der Weerdt, A.J.A. van der Weerdt

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Enamines of cyclodecanone and cyclododecanone (1a‐d) react with dimethyl acetylenedicarboxylate (DMAD) in an apolar solvent via (2 + 2) cycloaddition and conrotatory opening of the cyclobutene ring in 3 to give the cis,trans‐cycloalkadienes 5a‐d in yields of 44–85%. The compounds 5 do not undergo further thermal or photochemical transformation of the cis,trans moiety. In methanol, the enamines react with DMAD to give bicyclo[7.2.1]dodecene (8a) or bicyclo[9.2.1]tetradecene (8b and 8c) derivatives. These reactions take place via intramolecular nucleophilic addition of the enamine moiety to the α‐methoxycarbonyl group in 10, which is formed from the intermediate Michael adduct 9. The structure of 8b was determined by single‐crystal X‐ray analysis.

Original language	English
Pages (from-to)	380-386
Number of pages	7
Journal	Recueil des Travaux Chimiques des Pays‐Bas
Volume	105
Issue number	10
DOIs	https://doi.org/10.1002/recl.19861051011
Publication status	Published - 1986

Access to Document

10.1002/recl.19861051011

Cite this

Vos, G. J. M., Benders, P. H., Egberink, R. J. M., Reinhoudt, D. N., Harkema, S., van Hummel, G. J., van der Weerdt, A. J. A., & van der Weerdt, A. J. A. (1986). Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents. Recueil des Travaux Chimiques des Pays‐Bas, 105(10), 380-386. https://doi.org/10.1002/recl.19861051011

@article{a9e80e56618a49e88bbae1e18ab96a80,

title = "Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents",

abstract = "Enamines of cyclodecanone and cyclododecanone (1a‐d) react with dimethyl acetylenedicarboxylate (DMAD) in an apolar solvent via (2 + 2) cycloaddition and conrotatory opening of the cyclobutene ring in 3 to give the cis,trans‐cycloalkadienes 5a‐d in yields of 44–85%. The compounds 5 do not undergo further thermal or photochemical transformation of the cis,trans moiety. In methanol, the enamines react with DMAD to give bicyclo[7.2.1]dodecene (8a) or bicyclo[9.2.1]tetradecene (8b and 8c) derivatives. These reactions take place via intramolecular nucleophilic addition of the enamine moiety to the α‐methoxycarbonyl group in 10, which is formed from the intermediate Michael adduct 9. The structure of 8b was determined by single‐crystal X‐ray analysis.",

author = "G.J.M. Vos and P.H. Benders and R.J.M. Egberink and D.N. Reinhoudt and S. Harkema and {van Hummel}, G.J. and {van der Weerdt}, {A. J.A.} and {van der Weerdt}, A.J.A.",

year = "1986",

doi = "10.1002/recl.19861051011",

language = "English",

volume = "105",

pages = "380--386",

journal = "Recueil des travaux chimiques des Pays-Bas",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "10",

}

Vos, GJM, Benders, PH, Egberink, RJM , Reinhoudt, DN, Harkema, S, van Hummel, GJ, van der Weerdt, AJA & van der Weerdt, AJA 1986, 'Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents', Recueil des Travaux Chimiques des Pays‐Bas, vol. 105, no. 10, pp. 380-386. https://doi.org/10.1002/recl.19861051011

TY - JOUR

T1 - Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents

AU - Vos, G.J.M.

AU - Benders, P.H.

AU - Egberink, R.J.M.

AU - Reinhoudt, D.N.

AU - Harkema, S.

AU - van Hummel, G.J.

AU - van der Weerdt, A. J.A.

AU - van der Weerdt, A.J.A.

PY - 1986

Y1 - 1986

N2 - Enamines of cyclodecanone and cyclododecanone (1a‐d) react with dimethyl acetylenedicarboxylate (DMAD) in an apolar solvent via (2 + 2) cycloaddition and conrotatory opening of the cyclobutene ring in 3 to give the cis,trans‐cycloalkadienes 5a‐d in yields of 44–85%. The compounds 5 do not undergo further thermal or photochemical transformation of the cis,trans moiety. In methanol, the enamines react with DMAD to give bicyclo[7.2.1]dodecene (8a) or bicyclo[9.2.1]tetradecene (8b and 8c) derivatives. These reactions take place via intramolecular nucleophilic addition of the enamine moiety to the α‐methoxycarbonyl group in 10, which is formed from the intermediate Michael adduct 9. The structure of 8b was determined by single‐crystal X‐ray analysis.

AB - Enamines of cyclodecanone and cyclododecanone (1a‐d) react with dimethyl acetylenedicarboxylate (DMAD) in an apolar solvent via (2 + 2) cycloaddition and conrotatory opening of the cyclobutene ring in 3 to give the cis,trans‐cycloalkadienes 5a‐d in yields of 44–85%. The compounds 5 do not undergo further thermal or photochemical transformation of the cis,trans moiety. In methanol, the enamines react with DMAD to give bicyclo[7.2.1]dodecene (8a) or bicyclo[9.2.1]tetradecene (8b and 8c) derivatives. These reactions take place via intramolecular nucleophilic addition of the enamine moiety to the α‐methoxycarbonyl group in 10, which is formed from the intermediate Michael adduct 9. The structure of 8b was determined by single‐crystal X‐ray analysis.

UR - http://www.scopus.com/inward/record.url?scp=84987057624&partnerID=8YFLogxK

U2 - 10.1002/recl.19861051011

DO - 10.1002/recl.19861051011

M3 - Article

AN - SCOPUS:84987057624

VL - 105

SP - 380

EP - 386

JO - Recueil des travaux chimiques des Pays-Bas

JF - Recueil des travaux chimiques des Pays-Bas

SN - 0165-0513

IS - 10

ER -

Reactions of enamines of cyclodecanone and cyclododecanone with dimethyl acetylenedicarboxylate in apolar and in polar solvents

Abstract

Access to Document

Other files and links

Fingerprint

Cite this