137072-83-4

Upstream product

• 246876-11-9 1-phenyl-2-trimethylsilyl-1-benzophosphepine 1-oxide 
• 7345-79-1 2-bromocinnamic acid 
• 137072-82-3 1-phenyl-1-benzophosphepine 1-oxide 
• 154467-45-5 5-Phenyl-6-trimethylsilanyl-5H-5-phospha-benzocycloheptene 
• 119450-03-2 2,3-dibromo-3-(2-bromophenyl)propionic acid 
• 154467-44-4 (Z,Z)-1-bromo-4-(2-bromophenyl)-1-trimethylsilyl-1,3-butadiene 
• 154467-43-3 (Z)-1-(o-bromophenyl)-4-trimethylsilyl-1-buten-3-yne 
• 153140-75-1 1-bromo-2-[(Z)-2-bromoethenyl]benzene 

Downstream Products

• 137072-82-3 1-phenyl-1-benzophosphepine 1-oxide 
• 91-20-3 naphthalene 

Relevant academic research and scientific papers

A versatile synthesis of 1-benzoheteroepines containing group 14, 15, and 16 heavier elements via a common 1,6-dilithium intermediate

Fully unsaturated group 14 (Si, Ge, and Sn), group 15 (P, As, Sb, and Bi) and group 16 (S, Se, and Te) 2-trimethylsilyl-1-benzoheteroepines (16a- j), including the first isolated examples of bismepines, have been prepared by reaction of the corresponding electrophilic metal reagents (MX2 or MX4; M=group 14, 15, and 16 heavier elements) with the key 1,6-dilithium intermediate (9), generated from the common starting compound (Z,Z)-1-bromo- 4-(2-bromophenyl)-1-trimethylsilyl-1,3-butadiene (14) by treatment with tert- butyllithium. The trimethylsilyl group in 16b-j was readily removed by treatment with tetrabutylammonium fluoride to give the desired C- unsubstituted 1-benzoheteroepines (1b-j). Single crystal X-ray analyses of 1d (P) and 1f (Sb) revealed that the seven-membered rings exist in boat conformations with the heteroatoms at the bows. All obtained C-unsubstituted group 15 and 16 1-benzoheteroepines (1d-j) were thermolabile in solution towards heteroatom extrusion, while heteroepines (16d-j) having the bulky trimethylsilyl group at the 2-position were much more stable than 1d-j. The half-lives of 1d-j estimated from 1H-NMR spectral analysis indicate that the thermal stabilities of 1d-j decrease in the order 1f (Sb)>1d (P)>1e (As)>1g (Bi) in the group 15 heteroepines and 1j (Te)>1i (Se)>1h (S) in the group 16 heteroepines.

Studies on seven-membered heterocycles. XXXIV. Syntheses and reactions of 1-benzosilepines, 1-benzogermepines, 1-benzophosphepines, and 1-benzarsepines

Flash vacuum pyrolysis of 2a,7b-dihydrocyclobuta[b]-1-benzometalloles (6a-e), prepared from the corresponding 1-benzometalloles (3) containing Si, Ge, P, or As via three steps, resulted in valence isomerization with ring-opening to give 1,1-dimethyl-1-benzosilepine (7a), 1-methyl-1-phenyl-1-benzosilepine (7b), 1,1-dimethyl-1-benzogermepine (7c), 1-phenyl-1-benzophosphepine 1-oxide (7d), and 1-phenyl-1-benzarsepine 1-oxide (7e). The oxides (7d,e), on treatment with trichlorosilane, underwent deoxygenation to afford 1-phenyl-1-benzophosphepine (7f) and 1-phenyl-1-benzarsepine (7g). The 1-benzometallepines (7a-g) thus obtained are hitherto unknown heterocyclic ring compounds, and their thermal stabilities and several reactions were examined.

Synthesis of the Group 15 1-Benzoheteroepines, Dibenzoheteroepines and Dibenzoheteroepines involving the First Isolated Examples of Arsepines and Bismepines

The C-unsubstituted fully unsaturated Group 15 (P, As, Sb and Bi) 1-benzoheteroepines 6, dibenzoheteroepines 8 and dibenzoheteroepines 10 have been prepared from the dibromo compounds 3,7 and 9 having a 1,6-dibromohexatriene system, and their thermal stabilities have been examined.