Regarding oxaborole ring size (Scheme 3d), 5-( ), 6-( ), and 7-membered (18) rings could be accessed in generally good yield; however, the formation of an 8membered oxaborole (37) was not possible and instead the aryl BMIDA 38 was isolated. Intriguingly, 38 was isolated after the deprotection protocol, implying the BMIDA cleavage for 10, 18, and 19 was facilitated by the presence of the alcohol, for example, via dissociation of the N-methyl group on the BMIDA and association of the alcohol as shown in proposed intermediate 39. In the case of 37 and 38, increased flexibility/rotation seems to have prevented this hydrolysis.