TY - JOUR
T1 - Synthesis of an octamethyl-18-crown-6 derivative and the X-ray crystal structure of its 2:1 complex with borane-ammonia
AU - Alston, David R.
AU - Stoddart, J. Fraser
AU - Wolstenholme, John B.
AU - Allwood, Billy L.
AU - Williams, David J.
PY - 1985
Y1 - 1985
N2 - The synthesis of 2,2,3,3,11,11,12,12-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane (2) from pinacol (3) by a sequence of reactions (3→4→5→6+5→2) involving alkylation (3→ 4), ozonolysis and reduction (4→5), tosylation (5→6), and cyclisation (5+6→2) is reported. With borane-ammonia, the octamethyl-18-crown-6 derivative 2 forms a crystalline 2:1 complex, (BH3NH3)2 · 2. X-Ray crystallography reveals the two guest BH3NH3 molecules are hydrogen bonded in a centrosymmetric manner to the opposite faces of the host 2, which adopts an all-gauche (ag+a ag-a)3 conformation.
AB - The synthesis of 2,2,3,3,11,11,12,12-octamethyl-1,4,7,10,13,16-hexaoxacyclooctadecane (2) from pinacol (3) by a sequence of reactions (3→4→5→6+5→2) involving alkylation (3→ 4), ozonolysis and reduction (4→5), tosylation (5→6), and cyclisation (5+6→2) is reported. With borane-ammonia, the octamethyl-18-crown-6 derivative 2 forms a crystalline 2:1 complex, (BH3NH3)2 · 2. X-Ray crystallography reveals the two guest BH3NH3 molecules are hydrogen bonded in a centrosymmetric manner to the opposite faces of the host 2, which adopts an all-gauche (ag+a ag-a)3 conformation.
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U2 - 10.1016/S0040-4020(01)96617-7
DO - 10.1016/S0040-4020(01)96617-7
M3 - Article
AN - SCOPUS:0002888401
SN - 0040-4020
VL - 41
SP - 2923
EP - 2926
JO - Tetrahedron
JF - Tetrahedron
IS - 14
ER -