Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

L.C. Groenen; Leo C. Groenen; Bianca H.M. Ruel; Alessandro Casnati; P. Timmerman; Willem Verboom; Sybolt Harkema; Andrea Pochini; Rocco Ungaro; David Reinhoudt

doi:10.1016/S0040-4039(00)78816-2

Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

L.C. Groenen, Leo C. Groenen, Bianca H.M. Ruel, Alessandro Casnati, P. Timmerman, Willem Verboom, Sybolt Harkema, Andrea Pochini, Rocco Ungaro, David Reinhoudt

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

131 Citations (Scopus)

127 Downloads (Pure)

Abstract

In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.

Original language	Undefined
Pages (from-to)	2675-2678
Number of pages	4
Journal	Tetrahedron letters
Volume	0
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4039(00)78816-2
Publication status	Published - 1991

Keywords

METIS-106698
IR-12508

Access to Document

10.1016/S0040-4039(00)78816-2

K12508__

Cite this

@article{2fa519f6637f4ac5b13b0e394f156e0b,

title = "Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes",

abstract = "In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.",

keywords = "METIS-106698, IR-12508",

author = "L.C. Groenen and Groenen, {Leo C.} and Ruel, {Bianca H.M.} and Alessandro Casnati and P. Timmerman and Willem Verboom and Sybolt Harkema and Andrea Pochini and Rocco Ungaro and David Reinhoudt",

year = "1991",

doi = "10.1016/S0040-4039(00)78816-2",

language = "Undefined",

volume = "0",

pages = "2675--2678",

journal = "Tetrahedron letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "32",

}

TY - JOUR

T1 - Syn-1,2-dialkylated calix[4]arenes: general intermediates in the NaH/DMF tetraalkylation of calix[4]arenes

AU - Groenen, L.C.

AU - Groenen, Leo C.

AU - Ruel, Bianca H.M.

AU - Casnati, Alessandro

AU - Timmerman, P.

AU - Verboom, Willem

AU - Harkema, Sybolt

AU - Pochini, Andrea

AU - Ungaro, Rocco

AU - Reinhoudt, David

PY - 1991

Y1 - 1991

N2 - In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.

AB - In DMF or acetonitrile with NaH as a base at room temperature the tetraalkylation of calix[4]arenes 1a and 1b proceeds via the syn-1,2-disubstituted products to the tetraalkylated calix[4]arenes in the cone conformation. With KH as a base the tetraalkylated calix[4]arenes are predominantly formed in the partial cone conformation, and the reaction proceeds via both the syn-1,3-di and the syn-1,2-disubstituted products. Also the solvent influences the pathway via which tetraalkylation takes place. The syn-1,2-disubstituted calix[4]arenes 4-6 can be isolated in 15-55 % from the NaH/DMF or MeCN reactions when only 2.2 equiv of the electrophile are used.

KW - METIS-106698

KW - IR-12508

U2 - 10.1016/S0040-4039(00)78816-2

DO - 10.1016/S0040-4039(00)78816-2

M3 - Article

VL - 0

SP - 2675

EP - 2678

JO - Tetrahedron letters

JF - Tetrahedron letters

SN - 0040-4039

IS - 32

ER -