478359-02-3

Upstream product

• 478358-97-3 (12-ethoxycarbonylamino-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4⁽¹⁶⁾,5,7⁽¹⁵⁾,10⁽¹⁴⁾,11-hexaen-5-yl)-carbamic acid ethyl ester 
• 478358-95-1 [2.2]paracyclophane-4,15-dicarbonyl diazide 
• 478358-96-2 4,15-diisocyanato[2.2]paracyclophane 
• 74524-22-4 Ψ-m-carboxy-4-carboxy<2.2>paracyclophane 
• 56439-05-5 4,13-diamino<2.2>paracyclophane + 4,15-diamino<2.2>paracyclophane 

Downstream Products

• 4482-52-4 3,4-diphenyl-1,2-cyclobutanedicarboxylic acid 

Relevant academic research and scientific papers

4,15-Diamino[2.2]paracyclophane, a reusable template for topochemical reaction control in solution

An efficient synthesis of [2.2]paracyclophane-4,15-dicarboxylic acid (11) from [2.2]paracyclophane (8) has been developed. The diacid was converted via the diazide 14 into the 4,15-diisocyanato[2.2]paracyclophane (15), a versatile intermediate that could be transformed into many new pseudogeminally substituted derivatives of 8. For example, treatment of 15 with alcohols provided the carbamates 16 and 17. On treatment of 15 with diisopropylamine, the urea 18 was obtained, whereas reduction with lithium aluminium hydride afforded the cyclic urea 20. Hydrolysis of 15 furnished the diamine 19, which was used as a reusable spacer in a [2+2]photoaddition experiment. Thus, treatment of 19 with trans-cinnamoyl chloride (25) provided the bis(amide) 26, which on irradiation in acetone ring-closed to give the cyclobutane 28. Saponification of this yielded 3,4-diphenyl-1,2-cyclobutanedicarboxylic acid (27, β-truxinic acid) and returned the spacer system 19, both in quantitative yield. The X-ray structures of 15 and 20 are reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.