I′m not sure if it is exactly what you are searching, but maybe it helps:
mydata<-matrix(nrow=100, ncol=10, rnorm(1000, mean = 0, sd = 1))
rownames(mydata) <- paste0("id", 1:100) # some id for identification
# cluster objects and calculate dissimilarity matrix
cl <- cutree(hclust(
sim <- dist(mydata, diag = TRUE, upper=TRUE)), 5)
# combine results, take sum to aggregate dissimilarity
res <- data.frame(id=rownames(mydata),
cluster=cl, dis_sim=rowSums(as.matrix(sim)))
# order, lowest overall dissimilarity will be first
res <- res[order(res$dis_sim), ]
# split object
reslist <- split(res, f=res$cluster)
## takes first three items with highest overall dissim.
lapply(reslist, tail, n=3)
## returns id′s with highest overall dissimilarity, top 20%
lapply(reslist, function(x, p) tail(x, round(nrow(x)*p)), p=0.2)
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