TY - JOUR
T1 - Bimanes. 25. The Synthesis and Structures of Tricyclic Bimanes (μ-(Cn)-syn-(CH2,CH3 or C1)B)
AU - Marciano, Daniele
AU - Baud'huin, Michel
AU - Zinger, Baruch
AU - Goldberg, Israel
AU - Kosower, Edward M.
PY - 1990/12/1
Y1 - 1990/12/1
N2 - An effective synthesis of tricyclic bimanes (μ(Cn-syn-CM2,R1)B, R1 = CH3 or Cl)) (3a-g, = 1,2,3) from bis-acid chlorides via bis-3-keto esters and bis-pyrazolinones is described. The success of the synthesis is strong support for the previously proposed mechanism of bimane formation, via a diazacyclopentadienone and a diazoketene. Crystal structures for three chloro derivatives (3b-d, =1,2,3) reveal that the bimane dihedral ring angle and crystal packing details vary with the size of the third ring. Other spectroscopic properties (IR, UV, and NMR) vary with dihedral angle.
AB - An effective synthesis of tricyclic bimanes (μ(Cn-syn-CM2,R1)B, R1 = CH3 or Cl)) (3a-g, = 1,2,3) from bis-acid chlorides via bis-3-keto esters and bis-pyrazolinones is described. The success of the synthesis is strong support for the previously proposed mechanism of bimane formation, via a diazacyclopentadienone and a diazoketene. Crystal structures for three chloro derivatives (3b-d, =1,2,3) reveal that the bimane dihedral ring angle and crystal packing details vary with the size of the third ring. Other spectroscopic properties (IR, UV, and NMR) vary with dihedral angle.
UR - http://www.scopus.com/inward/record.url?scp=0342389765&partnerID=8YFLogxK
U2 - 10.1021/ja00176a036
DO - 10.1021/ja00176a036
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AN - SCOPUS:0342389765
SN - 0002-7863
VL - 112
SP - 7320
EP - 7328
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 20
ER -