TY - JOUR
T1 - Multiple Horner-Emmons cyclizations as a Route to Nonbenzenoid Aromatics. Synthesis of Polycyclic Dodecalenes
AU - Agranat, Israel
AU - Rabinovitz, Mordecai
AU - Shaw, Wu Chang
PY - 1979/2/1
Y1 - 1979/2/1
N2 - Quadruple Horner-Emmons cyclization reaction between the tetraaldehyde 6 and the bis phosphonate 7 afforded (9E, l4E, 24E, 29E)-hexabenzo[d, f, jk, o, q, uv]dodecalene (1a) and its 9E, 14Z, 24Z, 29E isomer (1b) in 4.2 and 0.4% yield, respectively. The analogous reaction between the tetrakis phosphonate 8 and the dialdehyde 4 afforded la in 0.3% yield. The double Horner-Emmons reaction between 4 and 7 afforded (9E, 19E)-tetrabenzo[a, c. g, i]cyclododecene (2a) in 8.0% yield. The advantages of the multiple Horner-Emmons reaction in the synthesis of polycyclic nonbenzenoid aromatics as compared with the conventional multiple Wittig reaction are discussed.
AB - Quadruple Horner-Emmons cyclization reaction between the tetraaldehyde 6 and the bis phosphonate 7 afforded (9E, l4E, 24E, 29E)-hexabenzo[d, f, jk, o, q, uv]dodecalene (1a) and its 9E, 14Z, 24Z, 29E isomer (1b) in 4.2 and 0.4% yield, respectively. The analogous reaction between the tetrakis phosphonate 8 and the dialdehyde 4 afforded la in 0.3% yield. The double Horner-Emmons reaction between 4 and 7 afforded (9E, 19E)-tetrabenzo[a, c. g, i]cyclododecene (2a) in 8.0% yield. The advantages of the multiple Horner-Emmons reaction in the synthesis of polycyclic nonbenzenoid aromatics as compared with the conventional multiple Wittig reaction are discussed.
UR - http://www.scopus.com/inward/record.url?scp=0000043459&partnerID=8YFLogxK
U2 - 10.1021/jo01326a010
DO - 10.1021/jo01326a010
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AN - SCOPUS:0000043459
SN - 0022-3263
VL - 44
SP - 1936
EP - 1941
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 12
ER -