A number of methods were tried in order to construct the strained four-carbon ring. A synthesis of 3,3-diphenylcyclobutanone
appeared in the literature.[2] The ketone was prepared in low yield by the reaction of
diphenylketene with 2 equiv of
diazomethane.[3] The latter synthesis, although low yielding, was used and the desired amines were prepared from 3,3-diphenylcyclobutanone.
^
abcdCarnmalm B, Rämsby S, Renyi AL, Ross SB, Ogren SO (January 1978). "Antidepressant agents. 9. 3,3-Diphenylcyclobutylamines, a new class of central stimulants". Journal of Medicinal Chemistry. 21 (1): 78–82.
doi:
10.1021/jm00199a014.
PMID22757.
^Wilt JW, Dabek RA, Welzel KC (1972). "Transannular neophyl rearrangement". The Journal of Organic Chemistry. 37 (3): 425–430.
doi:
10.1021/jo00968a022.
^Michejda CJ, Comnick RW (1975). "Acetolysis of 3,3-disubstituted cyclobutyl tosylates". The Journal of Organic Chemistry. 40 (8): 1046–1050.
doi:
10.1021/jo00896a010.
^Taylor EC, McKillop A, Hawks GH (1972). Michejda CJ, von Riesen DD, Comnick RW, Baumgarten HE (eds.). "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses. 52: 36.
doi:
10.15227/orgsyn.052.0036.
^Das M, Weissenfluh A, Ly N, Trudell ML (June 2020). "Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel-Crafts Arylation Conditions". The Journal of Organic Chemistry. 85 (12): 8209–8213.
doi:
10.1021/acs.joc.0c00454.
PMID32449343.
S2CID218873364.